GB793513A - Process for the preparation of ª†-4-chloro-2-methylphenoxybutyric acid and derivatives thereof - Google Patents

Process for the preparation of ª†-4-chloro-2-methylphenoxybutyric acid and derivatives thereof

Info

Publication number
GB793513A
GB793513A GB2619154A GB2619154A GB793513A GB 793513 A GB793513 A GB 793513A GB 2619154 A GB2619154 A GB 2619154A GB 2619154 A GB2619154 A GB 2619154A GB 793513 A GB793513 A GB 793513A
Authority
GB
United Kingdom
Prior art keywords
reaction
butyrolactone
entrainer
chloro
heating
Prior art date
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
GB2619154A
Inventor
Basil Jason Heywood
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.)
May and Baker Ltd
Original Assignee
May and Baker Ltd
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.)
Filing date
Publication date
Application filed by May and Baker Ltd filed Critical May and Baker Ltd
Priority to GB2619154A priority Critical patent/GB793513A/en
Priority to FR1139601D priority patent/FR1139601A/en
Publication of GB793513A publication Critical patent/GB793513A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring

Abstract

Gamma - 4 - chloro - 2 - methyl - phenoxybutyric acid is made by heating an alkali metal salt of 4-chloro-2-methyl-phenol with butyrolactone under substantially anhydrous conditions. The reaction is suitably carried out by treating the corresponding phenol with aqueous alkali, removing the water by co-distillation with an entrainer liquid, which may form an azeotropic mixture with water, adding butyrolactone to the resulting mixture of alkali metal phenoxide and entraining liquid, removing the entrainer by distillation and heating the residue at a temperature above 140 DEG C., preferably at 140-210 DEG C. to complete the reaction. The reaction may also be carried out by heating a mixture of the phenol in aqueous alkali with butyrolactone and the entrainer so that the azeotrope and the entrainer are successively distilled off, whereafter the temperature is raised to that required for reaction between the phenoxide and the butyrolactone. Suitable entraining liquids include chlorobenzene, white spirit, o-dichlorobenzene and xylene, the preferred liquids being alcohols boiling in the range 100-200 DEG C. such as n-butanol. The reaction between the alkali-metal phenoxide and the butyrolactone may also be carried out continuously by passing the reactants, optionally under pressure, through a heated tube. The free acid may be isolated from the alkali metal salt obtained as reaction product, by known methods. The products are used as selective herbicides. Specification 758,980 is referred to.
GB2619154A 1954-09-09 1954-09-09 Process for the preparation of ª†-4-chloro-2-methylphenoxybutyric acid and derivatives thereof Expired GB793513A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB2619154A GB793513A (en) 1954-09-09 1954-09-09 Process for the preparation of ª†-4-chloro-2-methylphenoxybutyric acid and derivatives thereof
FR1139601D FR1139601A (en) 1954-09-09 1955-09-08 Improved process for making aryloxylic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2619154A GB793513A (en) 1954-09-09 1954-09-09 Process for the preparation of ª†-4-chloro-2-methylphenoxybutyric acid and derivatives thereof

Publications (1)

Publication Number Publication Date
GB793513A true GB793513A (en) 1958-04-16

Family

ID=10239766

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2619154A Expired GB793513A (en) 1954-09-09 1954-09-09 Process for the preparation of ª†-4-chloro-2-methylphenoxybutyric acid and derivatives thereof

Country Status (2)

Country Link
FR (1) FR1139601A (en)
GB (1) GB793513A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1155139B (en) * 1958-08-16 1963-10-03 Basf Ag Process for the production of alkali salts of phenoxy fatty acids
US4749812A (en) * 1985-05-27 1988-06-07 Mitsui Toatsu Chemicals, Inc. N-(3-chloro-4-isopropylphenyl) carboxamide derivative and selective herbicide
US4764521A (en) * 1983-07-18 1988-08-16 Eli Lilly And Company Leukotriene antagonists and a method of use there as
CN115536514A (en) * 2022-09-15 2022-12-30 安徽兴隆化工有限公司 Production process and system of 2, 4-D butyric acid

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1126403B (en) * 1957-08-01 1962-03-29 Basf Ag Process for the preparation of 2-methyl-4-chlorophenoxybutyric acids or their alkali salts

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1155139B (en) * 1958-08-16 1963-10-03 Basf Ag Process for the production of alkali salts of phenoxy fatty acids
US4764521A (en) * 1983-07-18 1988-08-16 Eli Lilly And Company Leukotriene antagonists and a method of use there as
US4749812A (en) * 1985-05-27 1988-06-07 Mitsui Toatsu Chemicals, Inc. N-(3-chloro-4-isopropylphenyl) carboxamide derivative and selective herbicide
CN115536514A (en) * 2022-09-15 2022-12-30 安徽兴隆化工有限公司 Production process and system of 2, 4-D butyric acid

Also Published As

Publication number Publication date
FR1139601A (en) 1957-07-03

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