CA1174687A - 2-(-chloroethyl)-2-(4'-isobutylphenyl)-5,5-dimethyl-1, 3-dioxane - Google Patents

2-(-chloroethyl)-2-(4'-isobutylphenyl)-5,5-dimethyl-1, 3-dioxane

Info

Publication number: CA1174687A
Authority: CA; Canada
Prior art keywords: zinc; ketal; reaction; acid; salt
Prior art date: 1983-11-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000445574A

Other languages

English (en)

Inventor

Jerry A. Walker

Sanjay I. Amin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co

Original Assignee

Upjohn Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-11-24

Filing date

1984-01-18

Publication date

1984-09-18

1983-11-24 Priority claimed from CA000439426A external-priority patent/CA1164469A/fr

1984-01-18 Application filed by Upjohn Co filed Critical Upjohn Co

1984-01-18 Priority to CA000445574A priority Critical patent/CA1174687A/fr

1984-09-18 Application granted granted Critical

1984-09-18 Publication of CA1174687A publication Critical patent/CA1174687A/fr

Status Expired legal-status Critical Current

Links

150000002148 esters Chemical class 0.000 title abstract description 36
-1 zinc carboxylate Chemical class 0.000 title description 49
239000011701 zinc Substances 0.000 title description 47
229910052725 zinc Inorganic materials 0.000 title description 41
239000003054 catalyst Substances 0.000 title description 33
239000007788 liquid Substances 0.000 claims abstract description 22
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims abstract description 10
239000003377 acid catalyst Substances 0.000 claims abstract description 7
SISNYJLTSPWOOF-UHFFFAOYSA-N bis[2-(1-chloroethyl)-4-(2-methylpropyl)phenyl]methanone Chemical compound CC(Cl)C1=CC(CC(C)C)=CC=C1C(=O)C1=CC=C(CC(C)C)C=C1C(C)Cl SISNYJLTSPWOOF-UHFFFAOYSA-N 0.000 claims abstract description 5
239000003085 diluting agent Substances 0.000 claims abstract description 4
239000002253 acid Substances 0.000 abstract description 41
238000002360 preparation method Methods 0.000 abstract description 11
150000007513 acids Chemical class 0.000 abstract description 10
239000000543 intermediate Substances 0.000 abstract description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 70
238000000034 method Methods 0.000 description 42
239000000203 mixture Substances 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
230000008569 process Effects 0.000 description 29
239000000243 solution Substances 0.000 description 29
150000003839 salts Chemical class 0.000 description 27
239000000047 product Substances 0.000 description 22
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 18
229910052783 alkali metal Inorganic materials 0.000 description 16
229960001680 ibuprofen Drugs 0.000 description 16
239000002904 solvent Substances 0.000 description 16
239000006227 byproduct Substances 0.000 description 15
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 13
230000008707 rearrangement Effects 0.000 description 13
238000006460 hydrolysis reaction Methods 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
150000001340 alkali metals Chemical class 0.000 description 11
238000005755 formation reaction Methods 0.000 description 11
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
230000007062 hydrolysis Effects 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
150000002576 ketones Chemical class 0.000 description 9
235000005074 zinc chloride Nutrition 0.000 description 9
239000011592 zinc chloride Substances 0.000 description 9
229960001939 zinc chloride Drugs 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
239000012535 impurity Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
238000002955 isolation Methods 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
239000000376 reactant Substances 0.000 description 7
150000003751 zinc Chemical class 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
239000002585 base Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
238000010790 dilution Methods 0.000 description 6
239000012895 dilution Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 6
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 5
125000001188 haloalkyl group Chemical group 0.000 description 5
239000013067 intermediate product Substances 0.000 description 5
KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000005907 ketalization reaction Methods 0.000 description 4
229960002009 naproxen Drugs 0.000 description 4
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000002002 slurry Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000012267 brine Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
150000007942 carboxylates Chemical class 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000010931 ester hydrolysis Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
125000001475 halogen functional group Chemical group 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
239000000463 material Substances 0.000 description 3
229940073584 methylene chloride Drugs 0.000 description 3
CDBRNDSHEYLDJV-FVGYRXGTSA-M naproxen sodium Chemical compound [Na+].C1=C([C@H](C)C([O-])=O)C=CC2=CC(OC)=CC=C21 CDBRNDSHEYLDJV-FVGYRXGTSA-M 0.000 description 3
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000006462 rearrangement reaction Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
PTTPUWGBPLLBKW-UHFFFAOYSA-M sodium;2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound [Na+].CC(C)CC1=CC=C(C(C)C([O-])=O)C=C1 PTTPUWGBPLLBKW-UHFFFAOYSA-M 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
230000009466 transformation Effects 0.000 description 3
150000003752 zinc compounds Chemical class 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 2
GBVJENRFWPBYAC-UHFFFAOYSA-N 2-(1-chloroethyl)-5,5-dimethyl-2-[4-(2-methylpropyl)phenyl]-1,3-dioxane Chemical compound C1=CC(CC(C)C)=CC=C1C1(C(C)Cl)OCC(C)(C)CO1 GBVJENRFWPBYAC-UHFFFAOYSA-N 0.000 description 2
LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 2
SBNAWXAVNWGSHY-UHFFFAOYSA-N 2-chloro-1-(6-methoxynaphthalen-2-yl)propan-1-one Chemical compound C1=C(C(=O)C(C)Cl)C=CC2=CC(OC)=CC=C21 SBNAWXAVNWGSHY-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
206010001497 Agitation Diseases 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
238000005727 Friedel-Crafts reaction Methods 0.000 description 2
241001441571 Hiodontidae Species 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
125000002723 alicyclic group Chemical group 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000012062 aqueous buffer Substances 0.000 description 2
OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
238000007865 diluting Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001030 gas--liquid chromatography Methods 0.000 description 2
230000026030 halogenation Effects 0.000 description 2
238000005658 halogenation reaction Methods 0.000 description 2
150000003944 halohydrins Chemical class 0.000 description 2
231100001261 hazardous Toxicity 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
230000010354 integration Effects 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
235000011837 pasties Nutrition 0.000 description 2
238000012545 processing Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000013341 scale-up Methods 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000012546 transfer Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 2
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
QTCNKIZNNWURDV-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol Chemical compound OCC(C)(C)CO.OCC(C)(C)CO QTCNKIZNNWURDV-UHFFFAOYSA-N 0.000 description 1
UOPIOAUZQKSZRO-UHFFFAOYSA-N 2,4-dibromopentan-3-one Chemical class CC(Br)C(=O)C(C)Br UOPIOAUZQKSZRO-UHFFFAOYSA-N 0.000 description 1
KNIIVYSPWICSPD-UHFFFAOYSA-N 2-(1-bromoethyl)-2-(6-methoxynaphthalen-1-yl)-4-methyl-1,3-dioxane Chemical compound C=1C=CC2=CC(OC)=CC=C2C=1C1(C(C)Br)OCCC(C)O1 KNIIVYSPWICSPD-UHFFFAOYSA-N 0.000 description 1
OXDOSTYEVALKKT-UHFFFAOYSA-N 2-(1-bromopropyl)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane Chemical compound C=1C=C(OC)C=CC=1C1(C(Br)CC)OCC(C)(C)CO1 OXDOSTYEVALKKT-UHFFFAOYSA-N 0.000 description 1
UYQAQDFHDZOKGU-UHFFFAOYSA-N 2-(1-chloroethyl)-2-(3,4-dichlorophenyl)-4-ethyl-1,3-dioxane Chemical compound O1C(CC)CCOC1(C(C)Cl)C1=CC=C(Cl)C(Cl)=C1 UYQAQDFHDZOKGU-UHFFFAOYSA-N 0.000 description 1
LUNZPEGDDPLCQV-UHFFFAOYSA-N 2-(1-chloroethyl)-2-(6-methoxynaphthalen-1-yl)-5,5-dimethyl-1,3-dioxane Chemical compound C=1C=CC2=CC(OC)=CC=C2C=1C1(C(C)Cl)OCC(C)(C)CO1 LUNZPEGDDPLCQV-UHFFFAOYSA-N 0.000 description 1
JRDGRFYXEXLCGX-UHFFFAOYSA-N 2-(1-chloroethyl)-4,6-dimethyl-2-(3-phenoxyphenyl)-1,3-dioxane Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1C1(C(Cl)C)OC(C)CC(C)O1 JRDGRFYXEXLCGX-UHFFFAOYSA-N 0.000 description 1
SFCBVHHEXODMDU-UHFFFAOYSA-N 2-(4-butyl-2-methylphenyl)acetic acid Chemical compound C(CCC)C1=CC(=C(C=C1)CC(=O)O)C SFCBVHHEXODMDU-UHFFFAOYSA-N 0.000 description 1
UYHNNWQKLGPQQX-UHFFFAOYSA-N 2-[2-(2-methylpropyl)phenyl]propanoic acid Chemical class CC(C)CC1=CC=CC=C1C(C)C(O)=O UYHNNWQKLGPQQX-UHFFFAOYSA-N 0.000 description 1
ILLHORFDXDLILE-UHFFFAOYSA-N 2-bromopropanoyl bromide Chemical compound CC(Br)C(Br)=O ILLHORFDXDLILE-UHFFFAOYSA-N 0.000 description 1
XLSUKENQJDZSCX-UHFFFAOYSA-N 2-chloro-1-(3,4-dichlorophenyl)propan-1-one Chemical compound CC(Cl)C(=O)C1=CC=C(Cl)C(Cl)=C1 XLSUKENQJDZSCX-UHFFFAOYSA-N 0.000 description 1
ZLFKFRJPBMHBIK-UHFFFAOYSA-N 2-chloro-1-(3-phenoxyphenyl)propan-1-one Chemical compound CC(Cl)C(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZLFKFRJPBMHBIK-UHFFFAOYSA-N 0.000 description 1
FTNUZHDTKWNHGN-UHFFFAOYSA-N 2-chloro-1-(4-methoxyphenyl)propan-1-one Chemical compound COC1=CC=C(C(=O)C(C)Cl)C=C1 FTNUZHDTKWNHGN-UHFFFAOYSA-N 0.000 description 1
GIHSMBINQBEFLD-UHFFFAOYSA-N 2-chloro-1-[4-(2-methylpropyl)phenyl]propan-1-one Chemical compound CC(C)CC1=CC=C(C(=O)C(C)Cl)C=C1 GIHSMBINQBEFLD-UHFFFAOYSA-N 0.000 description 1
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
WDRFYIPWHMGQPN-UHFFFAOYSA-N 2-chloroisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Cl)C(=O)C2=C1 WDRFYIPWHMGQPN-UHFFFAOYSA-N 0.000 description 1
JEQDSBVHLKBEIZ-UHFFFAOYSA-N 2-chloropropanoyl chloride Chemical compound CC(Cl)C(Cl)=O JEQDSBVHLKBEIZ-UHFFFAOYSA-N 0.000 description 1
GNBPEYCZELNJMS-UHFFFAOYSA-N 2-methylbutane-1,3-diol Chemical compound CC(O)C(C)CO GNBPEYCZELNJMS-UHFFFAOYSA-N 0.000 description 1
DCNMHZIUXXXJIC-UHFFFAOYSA-N 2-phenylbutane-1,3-diol Chemical compound CC(O)C(CO)C1=CC=CC=C1 DCNMHZIUXXXJIC-UHFFFAOYSA-N 0.000 description 1
BPBDZXFJDMJLIB-UHFFFAOYSA-N 2-phenylpropane-1,3-diol Chemical compound OCC(CO)C1=CC=CC=C1 BPBDZXFJDMJLIB-UHFFFAOYSA-N 0.000 description 1
RBQLGIKHSXQZTB-UHFFFAOYSA-N 3-methylpentane-2,4-diol Chemical compound CC(O)C(C)C(C)O RBQLGIKHSXQZTB-UHFFFAOYSA-N 0.000 description 1
YPIFGDQKSSMYHQ-UHFFFAOYSA-M 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC([O-])=O YPIFGDQKSSMYHQ-UHFFFAOYSA-M 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
101100203596 Caenorhabditis elegans sol-1 gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000007836 KH2PO4 Substances 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000008365 aromatic ketones Chemical class 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000008901 benefit Effects 0.000 description 1
VTUOVBVMHPBQLX-UHFFFAOYSA-N benzene heptane Chemical compound CCCCCCC.C1=CC=CC=C1.C1=CC=CC=C1 VTUOVBVMHPBQLX-UHFFFAOYSA-N 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
208000012839 conversion disease Diseases 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
239000002044 hexane fraction Substances 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Chemical group 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000010451 perlite Substances 0.000 description 1
235000019362 perlite Nutrition 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000008055 phosphate buffer solution Substances 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000011175 product filtration Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000010926 purge Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000011160 research Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
CDBRNDSHEYLDJV-UHFFFAOYSA-M sodium;2-(6-methoxynaphthalen-2-yl)propanoate Chemical compound [Na+].C1=C(C(C)C([O-])=O)C=CC2=CC(OC)=CC=C21 CDBRNDSHEYLDJV-UHFFFAOYSA-M 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000445574A 1983-11-24 1984-01-18 2-(-chloroethyl)-2-(4'-isobutylphenyl)-5,5-dimethyl-1, 3-dioxane Expired CA1174687A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000445574A CA1174687A (fr)	1983-11-24	1984-01-18	2-(-chloroethyl)-2-(4'-isobutylphenyl)-5,5-dimethyl-1, 3-dioxane

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA000439426A CA1164469A (fr)	1983-11-24	1983-11-24	Preparation d'esters arylalcanoates via les cetales halo-1 alkyle aryle et comme catalyseurs les carboxylates de zinc
CA000445574A CA1174687A (fr)	1983-11-24	1984-01-18	2-(-chloroethyl)-2-(4'-isobutylphenyl)-5,5-dimethyl-1, 3-dioxane

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000439426A Division CA1164469A (fr)	1983-11-24	1983-11-24	Preparation d'esters arylalcanoates via les cetales halo-1 alkyle aryle et comme catalyseurs les carboxylates de zinc

Publications (1)

Publication Number	Publication Date
CA1174687A true CA1174687A (fr)	1984-09-18

Family

ID=25670186

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000445574A Expired CA1174687A (fr)	1983-11-24	1984-01-18	2-(-chloroethyl)-2-(4'-isobutylphenyl)-5,5-dimethyl-1, 3-dioxane

Country Status (1)

Country	Link
CA (1)	CA1174687A (fr)

1984
- 1984-01-18 CA CA000445574A patent/CA1174687A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-09-19	MKEC	Expiry (correction)
2003-11-24	MKEX	Expiry

Publication	Publication Date	Title
US4623736A (en)	1986-11-18	Arylalkanoic acid process improvement
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CA1174687A (fr)	1984-09-18	2-(-chloroethyl)-2-(4'-isobutylphenyl)-5,5-dimethyl-1, 3-dioxane
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CA1164469A (fr)	1984-03-27	Preparation d'esters arylalcanoates via les cetales halo-1 alkyle aryle et comme catalyseurs les carboxylates de zinc
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