CA1248125A - 5-HALOGENO-4H-1,3-DIOXIN-4-ONES; ESTERS .alpha.- HALOGENO-ACETOACETIQUES PREPARES A PARTIR DE CES COMPOSES; METHODES DE PREPARATION - Google Patents

5-HALOGENO-4H-1,3-DIOXIN-4-ONES; ESTERS .alpha.- HALOGENO-ACETOACETIQUES PREPARES A PARTIR DE CES COMPOSES; METHODES DE PREPARATION

Info

Publication number: CA1248125A
Authority: CA; Canada
Prior art keywords: halo; dioxin; compounds; preparation; alkali metal
Prior art date: 1984-06-11
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

CA000550976A

Other languages

English (en)

Inventor

Robert J. Clemens

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.)

Eastman Kodak Co

Original Assignee

Eastman Kodak 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.)

1984-06-11

Filing date

1987-11-03

Publication date

1989-01-03

1984-06-11 Priority claimed from US06/619,450 external-priority patent/US4633013A/en

1984-06-11 Priority claimed from US06/619,449 external-priority patent/US4582913A/en

1985-05-23 Priority claimed from CA000482152A external-priority patent/CA1234125A/fr

1987-11-03 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1987-11-03 Priority to CA000550976A priority Critical patent/CA1248125A/fr

1989-01-03 Application granted granted Critical

1989-01-03 Publication of CA1248125A publication Critical patent/CA1248125A/fr

Status Expired legal-status Critical Current

Links

150000002148 esters Chemical class 0.000 title claims abstract description 18
238000002360 preparation method Methods 0.000 title claims abstract description 16
238000000034 method Methods 0.000 title claims abstract description 12
150000001875 compounds Chemical class 0.000 title abstract description 20
-1 alkali metal alkoxide Chemical class 0.000 claims abstract description 20
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 16
229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
229910052794 bromium Inorganic materials 0.000 claims abstract description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
125000001475 halogen functional group Chemical group 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 21
125000003118 aryl group Chemical group 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
125000000217 alkyl group Chemical group 0.000 description 11
239000000460 chlorine Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 7
230000002140 halogenating effect Effects 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
229910001413 alkali metal ion Inorganic materials 0.000 description 4
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
239000000376 reactant Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
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 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
125000003107 substituted aryl group Chemical group 0.000 description 3
URHWMZVMAAUENN-UHFFFAOYSA-N 1,3-dioxin-4-one Chemical compound O=C1OCOC=C1 URHWMZVMAAUENN-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 2
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000008096 xylene Substances 0.000 description 2
JWYYQHWCGMDXOR-UHFFFAOYSA-N (4-nitrophenyl) 2-chloro-3-oxobutanoate Chemical compound CC(=O)C(Cl)C(=O)OC1=CC=C([N+]([O-])=O)C=C1 JWYYQHWCGMDXOR-UHFFFAOYSA-N 0.000 description 1
HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical compound C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 description 1
ODRZAZBEQWAOGU-UHFFFAOYSA-N 1,4-dioxin-2-one Chemical group O=C1COC=CO1 ODRZAZBEQWAOGU-UHFFFAOYSA-N 0.000 description 1
GUYVJLNKTIYUON-UHFFFAOYSA-N 2,2,2-trichloro-n-phenylacetamide Chemical compound ClC(Cl)(Cl)C(=O)NC1=CC=CC=C1 GUYVJLNKTIYUON-UHFFFAOYSA-N 0.000 description 1
XFRBXZCBOYNMJP-UHFFFAOYSA-N 2,2,6-trimethyl-1,3-dioxin-4-one Chemical compound CC1=CC(=O)OC(C)(C)O1 XFRBXZCBOYNMJP-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
BUYXYSZFWWMPCG-UHFFFAOYSA-N 5-bromo-2,2,6-trimethyl-1,3-dioxin-4-one Chemical compound CC1=C(Br)C(=O)OC(C)(C)O1 BUYXYSZFWWMPCG-UHFFFAOYSA-N 0.000 description 1
MFGNLRCIRUUKJY-UHFFFAOYSA-N 5-chloro-2,2,6-trimethyl-1,3-dioxin-4-one Chemical compound CC1=C(Cl)C(=O)OC(C)(C)O1 MFGNLRCIRUUKJY-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
238000006418 Brown reaction Methods 0.000 description 1
241000283986 Lepus Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000005323 carbonate salts Chemical class 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
NGJKQTAWMMZMEL-UHFFFAOYSA-N ethyl 2-bromo-3-oxobutanoate Chemical compound CCOC(=O)C(Br)C(C)=O NGJKQTAWMMZMEL-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
UJQMLHKSZKBMMO-UHFFFAOYSA-N n,n-diethylethanamine;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)CC UJQMLHKSZKBMMO-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

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

CA000550976A 1984-06-11 1987-11-03 5-HALOGENO-4H-1,3-DIOXIN-4-ONES; ESTERS .alpha.- HALOGENO-ACETOACETIQUES PREPARES A PARTIR DE CES COMPOSES; METHODES DE PREPARATION Expired CA1248125A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000550976A CA1248125A (fr)	1984-06-11	1987-11-03	5-HALOGENO-4H-1,3-DIOXIN-4-ONES; ESTERS .alpha.- HALOGENO-ACETOACETIQUES PREPARES A PARTIR DE CES COMPOSES; METHODES DE PREPARATION

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US619,449		1984-06-11
US06/619,450 US4633013A (en)	1984-06-11	1984-06-11	Preparation of α-haloacetoacetic esters
US06/619,449 US4582913A (en)	1984-06-11	1984-06-11	5-halo-4H-1,3-dioxin-4-one compounds
US619,450		1984-06-11
CA000482152A CA1234125A (fr)	1984-06-11	1985-05-23	5-HALOGENO-4H-1,3-DIOXIN-4-ONES; ESTERS .alpha.-HALOGENO- ACETO-ACETIQUES PREPARES A PARTIR DE CES COMPOSES; METHODE DE PREPARATION
CA000550976A CA1248125A (fr)	1984-06-11	1987-11-03	5-HALOGENO-4H-1,3-DIOXIN-4-ONES; ESTERS .alpha.- HALOGENO-ACETOACETIQUES PREPARES A PARTIR DE CES COMPOSES; METHODES DE PREPARATION

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000482152A Division CA1234125A (fr)	1984-06-11	1985-05-23	5-HALOGENO-4H-1,3-DIOXIN-4-ONES; ESTERS .alpha.-HALOGENO- ACETO-ACETIQUES PREPARES A PARTIR DE CES COMPOSES; METHODE DE PREPARATION

Publications (1)

Publication Number	Publication Date
CA1248125A true CA1248125A (fr)	1989-01-03

Family

ID=27167524

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000550976A Expired CA1248125A (fr)	1984-06-11	1987-11-03	5-HALOGENO-4H-1,3-DIOXIN-4-ONES; ESTERS .alpha.- HALOGENO-ACETOACETIQUES PREPARES A PARTIR DE CES COMPOSES; METHODES DE PREPARATION

Country Status (1)

Country	Link
CA (1)	CA1248125A (fr)

1987
- 1987-11-03 CA CA000550976A patent/CA1248125A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-01-03	MKEX	Expiry

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