GB764253A - Mixed organic-inorganic esters, the manufacture thereof and the conversion thereof into unsaturated esters and alcohols - Google Patents

Mixed organic-inorganic esters, the manufacture thereof and the conversion thereof into unsaturated esters and alcohols

Info

Publication number
GB764253A
GB764253A GB2586/55A GB258655A GB764253A GB 764253 A GB764253 A GB 764253A GB 2586/55 A GB2586/55 A GB 2586/55A GB 258655 A GB258655 A GB 258655A GB 764253 A GB764253 A GB 764253A
Authority
GB
United Kingdom
Prior art keywords
esters
unsaturated
octane
halo
give
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
GB2586/55A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB764253A publication Critical patent/GB764253A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • 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
    • C07C67/287—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • 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
    • C07C67/297—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups

Landscapes

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

Abstract

The invention comprises halogenated esters of 1 : (3) : 6-di- or trimethyl octane 1 : 3-diol, and dihalophosphato esters of the same compound, or containing in 3-position, the residue of a mono-valent non -OH- containing halogenated inorganic acid, and a process for preparing the products by treating the corresponding di-or tri-methyl octane diol with an acylating agent to give the ester, followed by an inorganic non-hydroxylic-halogen-containing esterifying agent to esterify the 3-group. The products may be further treated to convert them into unsaturated derivatives by heating in presence of an acid acceptor, hydrolysing to the alcohol and re-esterifying. In examples, the 3 : 7-dimethyl octane diol 1 : 3, obtainable from 6-methylheptanone-2 by the Darzens reaction via the 3 : 7-dimethyl 2 : 3-epoxy-ethyloctanoate by reduction with LiACH4, is esterified with acetylchloride, or benzoylchloride, followed by POCl3, or HCl, or HBr, to give the 1-acyl-3-halo- or halophosphato-3 : 7-dimethyl-octane; the 1-acetyl-3-halo or halophosphato derivatives on heating in pyridine are converted to mixtures of unsaturated 1-esters, which are hydrolysed to unsaturated 1-alcohols and re-esterified with formic acid, isobutyric anhydride, and benzoyl chloride, to give mixtures of unsaturated esters; a similar series of reactions is performed with 3 : 6 : 7-trimethyl octane-diol-1 : 3, to give mixed halo- or halo-phosphato-organic esters, convertible into the corresponding unsaturated esters, alcohols and new mono esters.
GB2586/55A 1954-01-29 1955-01-28 Mixed organic-inorganic esters, the manufacture thereof and the conversion thereof into unsaturated esters and alcohols Expired GB764253A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US764253XA 1954-01-29 1954-01-29

Publications (1)

Publication Number Publication Date
GB764253A true GB764253A (en) 1956-12-19

Family

ID=22131922

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2586/55A Expired GB764253A (en) 1954-01-29 1955-01-28 Mixed organic-inorganic esters, the manufacture thereof and the conversion thereof into unsaturated esters and alcohols

Country Status (1)

Country Link
GB (1) GB764253A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104803840A (en) * 2014-01-29 2015-07-29 中国科学院海洋研究所 Antibacterial monoterpene compounds, and preparation method and use thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104803840A (en) * 2014-01-29 2015-07-29 中国科学院海洋研究所 Antibacterial monoterpene compounds, and preparation method and use thereof

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