NL7905451A - Werkwijze ter bereiding van ethynylbenzeenderivaten. - Google Patents

Werkwijze ter bereiding van ethynylbenzeenderivaten. Download PDF

Info

Publication number: NL7905451A
Authority: NL; Netherlands
Prior art keywords: chlorine; hydrogen; phenyl; ethynylbenzene; formula
Prior art date: 1978-07-13

Application number

NL7905451A

Other languages

English (en)

Dutch (nl)

Original Assignee

Rorer Inc William H

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.)

1978-07-13

Filing date

1979-07-12

Publication date

1980-01-15

1979-07-12 Application filed by Rorer Inc William H filed Critical Rorer Inc William H

1980-01-15 Publication of NL7905451A publication Critical patent/NL7905451A/nl

Links

UEXCJVNBTNXOEH-OUBTZVSYSA-N ethynylbenzene Chemical class [13CH]#CC1=CC=CC=C1 UEXCJVNBTNXOEH-OUBTZVSYSA-N 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title claims 3
239000000460 chlorine Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 17
229910052801 chlorine Inorganic materials 0.000 claims description 17
238000000034 method Methods 0.000 claims description 16
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
-1 sulfonyl compound Chemical class 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
235000019445 benzyl alcohol Nutrition 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
239000011701 zinc Substances 0.000 claims description 3
AVUOTFYNSCPADS-UHFFFAOYSA-N 1-(4-ethynylphenyl)-2,4-difluorobenzene Chemical compound FC1=CC(F)=CC=C1C1=CC=C(C#C)C=C1 AVUOTFYNSCPADS-UHFFFAOYSA-N 0.000 claims description 2
RUTMLYUEOVNIKC-UHFFFAOYSA-N 1-chloro-2-(4-ethynylphenyl)benzene Chemical compound ClC1=CC=CC=C1C1=CC=C(C#C)C=C1 RUTMLYUEOVNIKC-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
229910052731 fluorine Inorganic materials 0.000 claims 2
239000011737 fluorine Substances 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
NAWUZMMAZOQEEA-UHFFFAOYSA-N 1-ethynyl-2-phenylbenzene Chemical compound C#CC1=CC=CC=C1C1=CC=CC=C1 NAWUZMMAZOQEEA-UHFFFAOYSA-N 0.000 claims 1
CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 claims 1
SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
230000026030 halogenation Effects 0.000 claims 1
238000005658 halogenation reaction Methods 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 22
239000000203 mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
MSDQNIRGPBARGC-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1CCCCC1 MSDQNIRGPBARGC-UHFFFAOYSA-N 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
0 *c(cc(cc1)C#C)c1N Chemical compound *c(cc(cc1)C#C)c1N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000007792 addition Methods 0.000 description 7
238000009835 boiling Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000007789 gas Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
230000001754 anti-pyretic effect Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
HSNQVADZWQJQJJ-UHFFFAOYSA-N 1-[4-(2,4-difluorophenyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=C(F)C=C1F HSNQVADZWQJQJJ-UHFFFAOYSA-N 0.000 description 1
PASUFCLLJYIBHP-UHFFFAOYSA-N 1-[4-(2-fluorophenyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1F PASUFCLLJYIBHP-UHFFFAOYSA-N 0.000 description 1
YETULFFXNIHQLK-UHFFFAOYSA-N 1-ethynyl-4-(2-fluorophenyl)benzene Chemical compound FC1=CC=CC=C1C1=CC=C(C#C)C=C1 YETULFFXNIHQLK-UHFFFAOYSA-N 0.000 description 1
VEWQNKABGVYDAZ-UHFFFAOYSA-N 1-ethynyl-4-(2-methylphenyl)benzene Chemical compound CC1=CC=CC=C1C1=CC=C(C#C)C=C1 VEWQNKABGVYDAZ-UHFFFAOYSA-N 0.000 description 1
HPOZHKBVIQCMSY-UHFFFAOYSA-N 2-(4-ethynylphenyl)-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1C1=CC=C(C#C)C=C1 HPOZHKBVIQCMSY-UHFFFAOYSA-N 0.000 description 1
SJKXKOQOXVNOFK-UHFFFAOYSA-N 2-chloro-1-cyclohexyl-4-ethylbenzene Chemical compound ClC1=CC(CC)=CC=C1C1CCCCC1 SJKXKOQOXVNOFK-UHFFFAOYSA-N 0.000 description 1
NTYNWUIIAXXZFO-UHFFFAOYSA-N 2-chloro-1-cyclohexyl-4-ethynylbenzene Chemical compound ClC1=CC(C#C)=CC=C1C1CCCCC1 NTYNWUIIAXXZFO-UHFFFAOYSA-N 0.000 description 1
KZWPOBXMZZFDFU-UHFFFAOYSA-N 2-chloro-4-ethynyl-1-phenylbenzene Chemical compound ClC1=CC(C#C)=CC=C1C1=CC=CC=C1 KZWPOBXMZZFDFU-UHFFFAOYSA-N 0.000 description 1
MBMMDZUOUNJYLS-UHFFFAOYSA-N 4-ethynyl-2-fluoro-1-phenylbenzene Chemical compound FC1=CC(C#C)=CC=C1C1=CC=CC=C1 MBMMDZUOUNJYLS-UHFFFAOYSA-N 0.000 description 1
AODRWJYAQARUQL-UHFFFAOYSA-N 4-ethynyl-2-methoxy-1-phenylbenzene Chemical compound COC1=CC(C#C)=CC=C1C1=CC=CC=C1 AODRWJYAQARUQL-UHFFFAOYSA-N 0.000 description 1
IFSYFPCAKLCYIZ-UHFFFAOYSA-N 4-ethynyl-2-methyl-1-phenylbenzene Chemical compound CC1=CC(C#C)=CC=C1C1=CC=CC=C1 IFSYFPCAKLCYIZ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
ANRONXYRHHJVMX-VZUCSPMQSA-N Clc(c(C/C=C/[ClH]I)ccc1)c1C1=CCCCC1 Chemical compound Clc(c(C/C=C/[ClH]I)ccc1)c1C1=CCCCC1 ANRONXYRHHJVMX-VZUCSPMQSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000008062 acetophenones Chemical class 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000010411 cooking Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
239000002027 dichloromethane extract Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
235000016804 zinc Nutrition 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/24—Preparation of ethers by reactions not forming ether-oxygen bonds by elimination of halogens, e.g. elimination of HCl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL7905451A 1978-07-13 1979-07-12 Werkwijze ter bereiding van ethynylbenzeenderivaten. NL7905451A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA307302		1978-07-13
CA307,302A CA1113125A (en)	1978-07-13	1978-07-13	Ethynylbenzenes

Publications (1)

Publication Number	Publication Date
NL7905451A true NL7905451A (nl)	1980-01-15

Family

ID=4111895

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7905451A NL7905451A (nl)	1978-07-13	1979-07-12	Werkwijze ter bereiding van ethynylbenzeenderivaten.

Country Status (6)

Country	Link
US (1)	US4267388A (it)
JP (1)	JPS584688B2 (it)
CA (1)	CA1113125A (it)
IT (1)	IT1121459B (it)
NL (1)	NL7905451A (it)
SE (1)	SE7906079L (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4686311A (en) *	1980-03-13	1987-08-11	Ethyl Corporation	Dehydrohalogenation of haloethyl brominated benzenes
WO1993007234A1 (en) *	1991-09-30	1993-04-15	F. Hoffmann-La Roche Ag	Halovinyl-derivatives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2060303A (en) *	1934-03-19	1936-11-10	Herbert P A Groll	Treatment of vinyl type monohalides
US3435075A (en) *	1965-06-15	1969-03-25	Merck & Co Inc	Process for preparing (halophenyl) alkyl ketone compounds
US3981932A (en) *	1972-07-03	1976-09-21	William H. Rorer, Inc.	Ethynylbenzene compounds and derivatives thereof
US4016214A (en) *	1974-11-12	1977-04-05	William H. Rorer, Inc.	Preparation of ethynylbenzenes
US4101591A (en) *	1975-05-14	1978-07-18	William H. Rorer, Inc.	Ethynylbenzene compounds and derivatives thereof

1978
- 1978-07-13 CA CA307,302A patent/CA1113125A/en not_active Expired
1979
- 1979-07-06 IT IT68412/79A patent/IT1121459B/it active
- 1979-07-12 SE SE7906079A patent/SE7906079L/xx not_active Application Discontinuation
- 1979-07-12 NL NL7905451A patent/NL7905451A/nl not_active Application Discontinuation
- 1979-07-12 US US06/056,984 patent/US4267388A/en not_active Expired - Lifetime
- 1979-07-13 JP JP54089167A patent/JPS584688B2/ja not_active Expired

Also Published As

Publication number	Publication date
IT1121459B (it)	1986-04-02
JPS5555124A (en)	1980-04-22
US4267388A (en)	1981-05-12
CA1113125A (en)	1981-11-24
SE7906079L (sv)	1980-01-14
IT7968412A0 (it)	1979-07-06
JPS584688B2 (ja)	1983-01-27

Legal Events

Date	Code	Title
1980-06-25	BA	A request for search or an international-type search has been filed
1982-03-01	BB	A search report has been drawn up
1985-01-01	A85	Still pending on 85-01-01
1985-03-01	BV	The patent application has lapsed

Publication	Publication Date	Title
RU2191770C2 (ru)	2002-10-27	Способ получения галоген-о-гидроксидифениловых соединений и ацильные соединения
JPH08268958A (ja)	1996-10-15	アルキル化芳香族カルボン酸およびハロゲン化アシルの製造方法
Fraser et al.	1988	The Chlorination of Ketones Using Trimeihylchlorosilane and Dimetwylsulfoxide With Bromide Ion Catalysis
US4093669A (en)	1978-06-06	Method for preparing trichloromethyl-trifluoromethyl-benzenes
JPS5949207B2 (ja)	1984-12-01	ジエンの製造方法
JPH0320375B2 (it)	1991-03-19
JP2739337B2 (ja)	1998-04-15	化合物の新規な製造方法
US4267388A (en)	1981-05-12	Process for producing ethynylbenzenes
JPH0323533B2 (it)	1991-03-29
JPH06263686A (ja)	1994-09-20	新規のハロゲン化非対称ベンゾフェノン類およびそれらの製造方法
US6433228B1 (en)	2002-08-13	Process for preparing 2-halogenated indan-1-ones
JP4258695B2 (ja)	2009-04-30	Ｏ−（ペルフルオロアルキル）ジベンゾフラニウム塩誘導体、その製造中間体、その製造中間体の製造方法、ペルフルオロアルキル化剤、並びにペルフルオロアルキル化方法
EP0887333B1 (en)	2001-11-14	Process for the production of halogeno-o-hydroxydiphenyl compounds
EP2452938A1 (en)	2012-05-16	Process for the preparation of 3-aroyl-5-aminobenzofuran derivatives
EP0331422A2 (en)	1989-09-06	Method of preparing 2-acylresorcinols
EP0290015B1 (en)	1991-10-16	Process for preparing macrocyclic 2-halogenoketones
JP3799580B2 (ja)	2006-07-19	Ｎ−置換−ｎ−スルホニルアミド類の製造方法
LU84748A1 (fr)	1983-12-05	Procede de preparation de derives de l'acide 2-thiophene acetique et produits intermediaires necessaires pour leur preparation
JP3128703B2 (ja)	2001-01-29	発色性化合物の製造方法及びその中間体類並びにそれらの製造方法
JPH04984B2 (it)	1992-01-09
JPH0640969A (ja)	1994-02-15	ジフルオロベンゼンの調製方法
JPWO1999006389A1 (ja)	2002-08-13	Ｏ−（ペルフルオロアルキル）ジベンゾフラニウム塩誘導体、その製造中間体、その製造中間体の製造方法、ペルフルオロアルキル化剤、並びにペルフルオロアルキル化方法
US3953520A (en)	1976-04-27	Chemical compounds and processes
JP3830206B2 (ja)	2006-10-04	α−ベンジルアクリル酸エステル類の製造方法
US5631406A (en)	1997-05-20	Chemical compounds