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GB1030491A - Trans-7-hydroxy-hept-2-enoic acid - Google Patents

Trans-7-hydroxy-hept-2-enoic acid

Info

Publication number
GB1030491A
GB1030491A GB1033561A GB1033561A GB1030491A GB 1030491 A GB1030491 A GB 1030491A GB 1033561 A GB1033561 A GB 1033561A GB 1033561 A GB1033561 A GB 1033561A GB 1030491 A GB1030491 A GB 1030491A
Authority
GB
United Kingdom
Prior art keywords
trans
enoic acid
hydroxy
ester
acid
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
GB1033561A
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.)
Glaxo Group Ltd
Original Assignee
Glaxo Group 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 Glaxo Group Ltd filed Critical Glaxo Group Ltd
Priority to GB1033561A priority Critical patent/GB1030491A/en
Publication of GB1030491A publication Critical patent/GB1030491A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl 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
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing 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
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • 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
    • C07C59/76—Unsaturated compounds containing keto groups

Landscapes

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

Abstract

The invention comprises trans-7-hydroxyhept-2-enoic acid and esters thereof with alcohols, and a process for preparing " queen substance," trans - 9 - oxo - dec - 2 - enoic acid by condensation of 5-hydroxy-pentanal, or its hemiacetate form 2-hydroxy-tetrahydropyran, or of 2,3-dihydropyran, with malonic acid in the presence of a base, to form trans-7-hydroxyhept-2-enoic acid, converting this compound, or an ester thereof, to a functional derivative of formula X-(CH2)4CH=CHCO2H or an ester thereof, followed by hydrolysis of the ester group if present, this functional derivative being then condensed with an acetoacetic ester salt of formula CH3COCHR-M, wherein R is a carboxylic ester group and M is an alkali metal or alkaline earth metal atom, X being an atom or group capable of splitting off with the atom M as a salt MX during condensation, and subjecting the product of formula CH3COCHR(CH2)4CH=CHCO2H to ketonic hydrolysis to remove the group R. Any 2 - tetrahydropyranylacetic acid formed in the initial condensation step may be converted (a) to trans-7-hydroxy-hept-2-enoic acid by reaction with zinc chloride and acetic acid, followed by hydrolysis of the 7-acetoxy group formed, or (b) to trans-7-bromo-hept-2-enoic acid (a functional derivative is defined above wherein X is a bromine atom) by reaction with hydrogen bromide.
GB1033561A 1961-03-21 1961-03-21 Trans-7-hydroxy-hept-2-enoic acid Expired GB1030491A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1033561A GB1030491A (en) 1961-03-21 1961-03-21 Trans-7-hydroxy-hept-2-enoic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1033561A GB1030491A (en) 1961-03-21 1961-03-21 Trans-7-hydroxy-hept-2-enoic acid

Publications (1)

Publication Number Publication Date
GB1030491A true GB1030491A (en) 1966-05-25

Family

ID=9965967

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1033561A Expired GB1030491A (en) 1961-03-21 1961-03-21 Trans-7-hydroxy-hept-2-enoic acid

Country Status (1)

Country Link
GB (1) GB1030491A (en)

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