GB1421129A - Process for preparing heptadec-16-en-1,2,4-triol derivatives - Google Patents
Process for preparing heptadec-16-en-1,2,4-triol derivativesInfo
- 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
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.
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)
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 |
-
1972
- 1972-03-03 GB GB1009272A patent/GB1421129A/en not_active Expired
Cited By (4)
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 |