GB859568A - 2-substituted-2,6-dimethyl octane derivatives - Google Patents

2-substituted-2,6-dimethyl octane derivatives

Info

Publication number
GB859568A
GB859568A GB12759/59A GB1275959A GB859568A GB 859568 A GB859568 A GB 859568A GB 12759/59 A GB12759/59 A GB 12759/59A GB 1275959 A GB1275959 A GB 1275959A GB 859568 A GB859568 A GB 859568A
Authority
GB
United Kingdom
Prior art keywords
dimethyl
group
octane
give
chlorhydrin
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
GB12759/59A
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.)
Akzo Nobel Paints LLC
Original Assignee
Glidden Co
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 Glidden Co filed Critical Glidden Co
Publication of GB859568A publication Critical patent/GB859568A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
    • 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
    • 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
    • C07C45/58—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 three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds

Abstract

The invention comprises 2,6-dimethyloctane derivatives having the general formula : <FORM:0859568/IV(b)/1> in which Y is the group <FORM:0859568/IV(b)/2> or the group <FORM:0859568/IV(b)/3> in which one group A is a hydroxyl radical and the other is a halogen radical, and x is a halogen, hydroxyl, alkoxy or acyloxy (derived from a carboxylic acid) group. The compounds of the above formula in which Y is the group <FORM:0859568/IV(b)/4> may be prepared by (a) epoxidising a compound of formula : <FORM:0859568/IV(b)/5> for example, by treating with a per-acid or with gaseous oxygen, or, by forming the corresponding halohydrin and submitting it to dehydrohalogenation ; and (b) if desired, when X is a halogen, alkoxy or acyloxy radical, hydrolysing it to convert it to a hydroxyl group. If desired the oxirane group may be thermally isomerised, preferably at a temperature above 200 DEG C. to give the aldehyde group -CH2CHO. When X is an acyloxy radical the hydrolysis is carried out in an acidic or basic medium ; when X is a halogen radical it is carried out in a basic medium and when X is alkoxy it is preferably carried out in an acidic medium. The process is particularly suitable for producing 2-hydroxy-dihydrocitronellal from <FORM:0859568/IV(b)/6> by producing <FORM:0859568/IV(b)/7> and thermally isomerising it to the corresponding aldehyde. Some citronellal may also be formed as a result of the heat treatment. The halohydrins may be obtained by treating the unsaturated starting compound with hypochlorous or hypobromous acid. The chlorhydrin is converted to the corresponding epoxy compound by heating it with a base, e.g. caustic soda. If the 2-substituent is a halide group, some dehydrohalogenation takes place resulting in the formation of the corresponding unsaturated compound. The chlorhydrin can be converted to the aldehyde in one stage by heating it, preferably with a base, at a sufficiently high temperature. If heated without a base until decomposition takes place 2-hydroxy-2,6-dimethyl-octane-7,8-chlorhydrin yields a mixture of 2,6-dimethyl-1-octen-8-al and 8-chlor-2,6-dimethyl-1,7-octadiene. A small amount of 2-hydroxy-2,6-dimethyl-octane-7-one is also formed and this may be dehydrated to give the corresponding unsaturated ketone. When 2,6-dimethyl-7-octene-2-ol is subjected to hypochlorination 7,8-dichlor-2,6-dimethyl-octane-2-ol is also formed. This may be dechlorinated by means of sodium and alcohol to give 2,6-dimethyl-7-octene-2-ol which may be recycled for subsequent hypochlorous acid treatment. The 7,8-dichloro-2,6-dimethyl-octane-2-ol may be dehydrated to give 7,8-dichloro-2,6-dimethyl-2-octene. The 7,8-dichloro-2,6-dimethyl-octane-2-ol may be dehydrohalogenated to give an alcohol which is probably 2,6-dimethyl-6,7-octadiene-2-ol. Similar results are obtained when the bromhydrin is formed instead of the chlorhydrin.
GB12759/59A 1956-04-09 1957-04-03 2-substituted-2,6-dimethyl octane derivatives Expired GB859568A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US859568XA 1956-04-09 1956-04-09

Publications (1)

Publication Number Publication Date
GB859568A true GB859568A (en) 1961-01-25

Family

ID=22195075

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12759/59A Expired GB859568A (en) 1956-04-09 1957-04-03 2-substituted-2,6-dimethyl octane derivatives

Country Status (1)

Country Link
GB (1) GB859568A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3963648A (en) * 1972-09-08 1976-06-15 Bush Boake Allen Limited Perfume chemicals
WO2013053787A1 (en) 2011-10-11 2013-04-18 Givaudan Sa Process for the preparation of methoxymelonal

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3963648A (en) * 1972-09-08 1976-06-15 Bush Boake Allen Limited Perfume chemicals
WO2013053787A1 (en) 2011-10-11 2013-04-18 Givaudan Sa Process for the preparation of methoxymelonal
US9701606B2 (en) 2011-10-11 2017-07-11 Givaudan S.A. Process for the preparation of methoxymelonal

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