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GB813018A - A method for the preparation of isomeric tertiary alcohols - Google Patents

A method for the preparation of isomeric tertiary alcohols

Info

Publication number
GB813018A
GB813018A GB13685/57A GB1368557A GB813018A GB 813018 A GB813018 A GB 813018A GB 13685/57 A GB13685/57 A GB 13685/57A GB 1368557 A GB1368557 A GB 1368557A GB 813018 A GB813018 A GB 813018A
Authority
GB
United Kingdom
Prior art keywords
ionone
dihydro
per cent
geranyl
trimethyl
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
GB13685/57A
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
Publication of GB813018A publication Critical patent/GB813018A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • 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
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
    • C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

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

Abstract

Mixtures of the three isomeric 1,1,6-trimethyl - 6 - hydroxyoctahydronaphthalenes are prepared by cyclization of dihydro-g -ionone, itself formed in situ by treating dihydro-a -ionone with phosphoric acid containing pyridine (preferably 2-8 per cent by weight.) The dihydro-a -ionone may itself be produced in situ by using geranyl-acetone as the starting material. Another alcohol having the formula <FORM:0813018/IV (b)/1> is also produced in yields up to 20 per cent by direct cyclisation of dihydro-a -ionone, and is eliminated from the product of the reaction by distillation. In examples: (1) dihydro-a -ionone in benzene is added to cooled 84 per cent phosphonic acid containing pyridine, the mixture stirred under nitrogen, poured into water, extracted with petroleum ether and fractionated in vacuo; the alcoholic components are separated by treatment with ethyl borate, the borate compounds decomposed with KOH and the product again fractionated, giving a mixture of the three 1,1,6-trimethyl-6-hydroxy-octahydronaphthalenes; (2) as in (1), using a higher percentage of pyridine; (3) as in (1), employing geranyl-acetone as starting material.
GB13685/57A 1956-06-13 1957-04-30 A method for the preparation of isomeric tertiary alcohols Expired GB813018A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH813018X 1956-06-13

Publications (1)

Publication Number Publication Date
GB813018A true GB813018A (en) 1959-05-06

Family

ID=4538685

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13685/57A Expired GB813018A (en) 1956-06-13 1957-04-30 A method for the preparation of isomeric tertiary alcohols

Country Status (1)

Country Link
GB (1) GB813018A (en)

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