GB587545A - Production of mono- and di-ª‡-substituted ª‡-alkoxy-acetic acids and of ª‡,ª‰-unsaturated esters therefrom - Google Patents

Production of mono- and di-ª‡-substituted ª‡-alkoxy-acetic acids and of ª‡,ª‰-unsaturated esters therefrom

Info

Publication number
GB587545A
GB587545A GB1271544A GB1271544A GB587545A GB 587545 A GB587545 A GB 587545A GB 1271544 A GB1271544 A GB 1271544A GB 1271544 A GB1271544 A GB 1271544A GB 587545 A GB587545 A GB 587545A
Authority
GB
United Kingdom
Prior art keywords
acid
isobutyl
alkoxy
prepared
ccl3
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
GB1271544A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB1271544A priority Critical patent/GB587545A/en
Publication of GB587545A publication Critical patent/GB587545A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/34—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/093—Preparation of carboxylic acids or their salts, halides or anhydrides by hydrolysis of —CX3 groups, X being halogen
    • 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
    • C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/08—Saturated compounds containing ether groups, groups, groups, or groups
    • C07C62/10—Saturated compounds containing ether groups, groups, groups, or groups with a six-membered ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Mono- and dia -substituted a -alkoxy acetic acids of the general formul R1.CH2.CH(OR4).COOH, R1R2CH.CH(OR4).COOH, R1CH2.CR3 (OR4).COOH and R1R2CH.CR3(OR4).COOH in which R1, R2, R3 and R4 represent hydro carbon radicals of aliphatic nature and in the third formula, R1 and R3 may form a ring with the a -carbon of the acid, are prepared by treating halogenated alcohols having the general formul R1.CH2.CH(OH).CCl3, R1R2.CH.CH (OH).CCl3, R1.CH2CR3(OH).CCl3 and R1R2 CH.CR3(OH).CCl3, such as are available, for example, by the process described in Specification 587,275 with a solution of an alkali metal hydroxide in an aliphatic alcohol of the formula R4OH and acidifying the product. The acids obtained may be converted into the corresponding amides and phenylhydrazides and into primary or secondary esters by esterification, in presence of an esterification catalyst, with the corresponding alcohols. These esters are converted into a b unsaturated esters by dealkoxylation on treating with a dehydrating agent either catalytically or non-catalytically, and conveniently by heating with phosphorus pentoxide and preferably in presence of polymerization inhibitors. The products have the general formul R1CH : CR3COOR5, R1CH : CHCOOR5, R1R2C : CHCOOR5 and R1R2 : CR3COOR5, or when, in the first formula, R1 and R3 form a ring, <FORM:0587545/IV/1> , where R5 is the radical of a primary or secondary alcohol used in the esterification. The unsaturated esters may be prepared in a single operation by preparing the alkoxy acids as above and heating the resulting alcoholic solution thereof in the presence of concentrated sulphuric acid. In examples: (1) a -isobutoxy methyl ethyl acetic acid was prepared by reacting trichloro-tertiary amyl alcohol (obtained from methyl ethyl ketone and chloroform) with an isobutyl alcohol solution of potassium hydroxide and acidifying with hydrochloric acid; the isobutyl ester, as well as some of the corresponding unsaturated ester isobutyl tiglate, were prepared by esterification of the alkoxy acid in the presence of sulphuric acid and tannic acid; the ester of the alkoxy acid was converted to isobutyl tiglate by heating with phosphorus pentoxide, hydrolysed, and the free tiglic acid converted to the dibromide; (2) 1-isobutoxy-cyclohexane-1-carboxylic acid, the isobutyl ester and isobutyl cyclohexene-1-carboxylate were prepared likewise from 1-trichloromethyl-cyclohexanol; and a -isobutoxy-b -ethyl heptoic acid, its isobutyl ester and isobutyl b -ethyl heptenoate from 1.1.1-trichloro-3-ethyl-heptanol-2. Specifications 578,082 and 584,607 also are referred to.
GB1271544A 1944-07-04 1944-07-04 Production of mono- and di-ª‡-substituted ª‡-alkoxy-acetic acids and of ª‡,ª‰-unsaturated esters therefrom Expired GB587545A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1271544A GB587545A (en) 1944-07-04 1944-07-04 Production of mono- and di-ª‡-substituted ª‡-alkoxy-acetic acids and of ª‡,ª‰-unsaturated esters therefrom

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1271544A GB587545A (en) 1944-07-04 1944-07-04 Production of mono- and di-ª‡-substituted ª‡-alkoxy-acetic acids and of ª‡,ª‰-unsaturated esters therefrom

Publications (1)

Publication Number Publication Date
GB587545A true GB587545A (en) 1947-04-29

Family

ID=10009777

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1271544A Expired GB587545A (en) 1944-07-04 1944-07-04 Production of mono- and di-ª‡-substituted ª‡-alkoxy-acetic acids and of ª‡,ª‰-unsaturated esters therefrom

Country Status (1)

Country Link
GB (1) GB587545A (en)

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