GB998354A - Improvements in or relating to a process for the manufacture of manool derivatives - Google Patents

Improvements in or relating to a process for the manufacture of manool derivatives

Info

Publication number
GB998354A
GB998354A GB91062A GB91062A GB998354A GB 998354 A GB998354 A GB 998354A GB 91062 A GB91062 A GB 91062A GB 91062 A GB91062 A GB 91062A GB 998354 A GB998354 A GB 998354A
Authority
GB
United Kingdom
Prior art keywords
epoxy
ketone
manool
epoxide
group
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
GB91062A
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 GB998354A publication Critical patent/GB998354A/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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • 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
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • 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
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Epoxy Compounds (AREA)

Abstract

The invention comprises manool epoxide which may be prepared by treating manool with an organic per-acid. The manool used is preferably of natural origin. The manool epoxide may be converted into an epoxy ketone by several methods and the epoxy ketone formed may be subjected to internal ketalization between the epoxy group and the ketone group. The epoxide may be converted to an epoxy ketone by subjecting it to the action of an alkali metal periodate in the presence of a hydroxylating agent, e.g. osmium tetroxide or an alkaline permanganate; the hydroxylating agent causes the intermediate formation of an epoxytriol which is immediately oxidized to the epoxyketone as follows:- <FORM:0998354/C2/1> Alternatively the manool epoxide may be treated with osmium tetroxide to form a complex of formula <FORM:0998354/C2/2> decomposing this complex, preferably by treatment with mannitol in the presence of a base, to give the epoxy-triol shown above and oxidizing this, for example, with periodic acid or one of its salts. In another method the monoepoxide may be ozonized to give the compound <FORM:0998354/C2/3> which can be converted to the epoxy-ketone by decomposing with water in the presence of dioxane and an alkali. The epoxy-ketone may be subjected to intramolecular ketalisation between the ketone group and the epoxide group. This may be achieved by heating the epoxy-ketone in an organic medium in the presence of an acid catalyst. The product is a mixture of stereoisomeric internal ketals having the formulae <FORM:0998354/C2/4>
GB91062A 1961-01-12 1962-01-10 Improvements in or relating to a process for the manufacture of manool derivatives Expired GB998354A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH35961A CH408956A (en) 1961-01-12 1961-01-12 Process for the preparation of polycyclic internal ketals

Publications (1)

Publication Number Publication Date
GB998354A true GB998354A (en) 1965-07-14

Family

ID=4185212

Family Applications (1)

Application Number Title Priority Date Filing Date
GB91062A Expired GB998354A (en) 1961-01-12 1962-01-10 Improvements in or relating to a process for the manufacture of manool derivatives

Country Status (3)

Country Link
CH (1) CH408956A (en)
FR (1) FR1310242A (en)
GB (1) GB998354A (en)

Also Published As

Publication number Publication date
CH408956A (en) 1966-03-15
FR1310242A (en) 1963-03-06

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