GB1421129A - Process for preparing heptadec-16-en-1,2,4-triol derivatives - Google Patents

Process for preparing heptadec-16-en-1,2,4-triol derivatives

Info

Publication number
GB1421129A
GB1421129A GB1009272A GB1009272A GB1421129A GB 1421129 A GB1421129 A GB 1421129A GB 1009272 A GB1009272 A GB 1009272A GB 1009272 A GB1009272 A GB 1009272A GB 1421129 A GB1421129 A GB 1421129A
Authority
GB
United Kingdom
Prior art keywords
reacting
ene
derivative
heptadec
diacetoxyheptadec
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
GB1009272A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to GB1009272A priority Critical patent/GB1421129A/en
Publication of GB1421129A publication Critical patent/GB1421129A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/04—Acyclic alcohols with carbon-to-carbon triple bonds
    • C07C33/042—Acyclic alcohols with carbon-to-carbon triple bonds with only one triple bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/18—Acetic acid esters of trihydroxylic compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1421129 Preparation of heptadec-16-en-1,2,4- triol derivatives SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ NV 1 March 1973 [3 March 1972] 10092/72 Heading C2C The invention comprises 1,2-diacetoxyheptadec-16-en-4-ol and the preparation of compounds CH 2 = CH(CH 2 ) 11 CH(OR 1 )CH 2 CH(OR 2 )- CH 2 (OR 3 )<SP>1</SP> 1 (1), where R 1 , R 2 and R 3 are hydrogen or acyl (preferably acetyl), by reacting a metal derivative of a halide CH 2 =CH(CH 2 ) 11 - Hal (2), where Hal is Cl, Br or I, with a butyraldehyde derivative R 4 O.CH 2 CH(OR 5 )CH 2 CHO (3), where R 4 and R 5 are acyl and optionally saponifying and/or esterifying the product. 1-Bromotridec-12-ene is made by reacting 1- hydroxyundec-10-ene with PCl 3 , reacting the Grignard complex of the resulting 1-bromoundec-10-ene with ethylene oxide and reacting the formed l-hydroxytridec-12-ene with PCl 3 . 3,4-Diacetorybutyraldehyde and 4-acetorycrotonaldehyde (as by-product) are formed by reacting the Grignard derivative of allyl bromide with ethyl orthoformate, reacting the formed 4,4-diethoxybut-1-ene with KMnO 4 , esterifying the produced 4,4-diethoxybutan-1,2-diol and treating the formed 1,2-diacetoxy-4,4-diethoxybutane with 90% acetic acid. A plant growth retardant composition comprises 1,2 - diacetoxyheptadec - 16 - en - 4 - ol and a carrier and/or surfactant.
GB1009272A 1972-03-03 1972-03-03 Process for preparing heptadec-16-en-1,2,4-triol derivatives Expired GB1421129A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1009272A GB1421129A (en) 1972-03-03 1972-03-03 Process for preparing heptadec-16-en-1,2,4-triol derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1009272A GB1421129A (en) 1972-03-03 1972-03-03 Process for preparing heptadec-16-en-1,2,4-triol derivatives

Publications (1)

Publication Number Publication Date
GB1421129A true GB1421129A (en) 1976-01-14

Family

ID=9961337

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1009272A Expired GB1421129A (en) 1972-03-03 1972-03-03 Process for preparing heptadec-16-en-1,2,4-triol derivatives

Country Status (1)

Country Link
GB (1) GB1421129A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10493057B2 (en) * 2015-09-23 2019-12-03 Instituto Tecnologico Y De Estudios Superiores De Monterrey Acetogenin molecules having antiplatelet and/or antithrombic activities, and methods and compositions thereof
US10575521B2 (en) 2010-08-09 2020-03-03 Instituto Technologico Y De Estudios Superiores De Monterrey Antimicrobial, antibacterial and spore germination inhibiting activity from an avocado extract enriched in bioactive compounds
US10932484B2 (en) 2016-10-19 2021-03-02 Instituto Tecnologico Y De Estudios Superiores De Monterrey Inhibitory activity of acetogenins against Listeria monocytogenes

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10575521B2 (en) 2010-08-09 2020-03-03 Instituto Technologico Y De Estudios Superiores De Monterrey Antimicrobial, antibacterial and spore germination inhibiting activity from an avocado extract enriched in bioactive compounds
US10582707B2 (en) 2010-08-09 2020-03-10 Instituto Tecnologico Y De Estudios Superiores De Monterrey Antimicrobial antibacterial and spore germination inhibiting activity from an avocado extract enriched in bioactive compounds
US10493057B2 (en) * 2015-09-23 2019-12-03 Instituto Tecnologico Y De Estudios Superiores De Monterrey Acetogenin molecules having antiplatelet and/or antithrombic activities, and methods and compositions thereof
US10932484B2 (en) 2016-10-19 2021-03-02 Instituto Tecnologico Y De Estudios Superiores De Monterrey Inhibitory activity of acetogenins against Listeria monocytogenes

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee