GB875685A - Allo-ocimenol and its derivatives - Google Patents

Allo-ocimenol and its derivatives

Info

Publication number
GB875685A
GB875685A GB2854858A GB2854858A GB875685A GB 875685 A GB875685 A GB 875685A GB 2854858 A GB2854858 A GB 2854858A GB 2854858 A GB2854858 A GB 2854858A GB 875685 A GB875685 A GB 875685A
Authority
GB
United Kingdom
Prior art keywords
allo
ocimenol
ocimene
tetrahydro
hydrogen chloride
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
GB2854858A
Inventor
Ernst Theodore Theimer
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.)
International Flavors and Fragrances Inc
Original Assignee
International Flavors and Fragrances Inc
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 International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc
Priority to GB2854858A priority Critical patent/GB875685A/en
Publication of GB875685A publication Critical patent/GB875685A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
    • C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
    • 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
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
    • 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
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • 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

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises a mixture of conjugated diolefinic tertiary alcohols having D15 = 0.877 and n20D = 1.4913 and having the structural formula <FORM:0875685/IV (b)/1> where one of the symbols R1 and R2 is methyl and the other is ethyl and a process for producing allo-ocimenol having the empirical formula C10H18O and derivatives thereof which comprises reacting hydrogen chloride with allo-ocimene in the proportion of not more than 1 mole of hydrogen chloride per mole of allo-ocimene, hydrolysing the resulting allo-ocimene hydrochloride, prior to any substantial decomposition of same, with an aqueous base in the presence of a non-ionic emulsifying agent, and isolating allo-ocimenol, and then if desired, hydrogenating the allo-ocimenol to tetrahydro allo-ocimenol and further, if desired, esterifying the tetrahydro - allo-ocimenol. The hydrochlorination and hydrolysis steps are preferably carried out continuously. In examples technical allo-ocimene is hydrochlorinated with anhydrous hydrogen chloride alone or diluted with dry nitrogen and the resulting hydrochloride run directly into an aqueous solution of sodium hydroxide and the emulsifying agent which is then stirred 20 hours at room temperature and allo-ocimenol recovered by steam distillation. The alcohol so obtained is then hydrogenated over Raney nickel to give tetrahydro-allo-ocimenol which is converted to its acetate by treatment with acetic anhydride. The compounds find application as perfume bases.
GB2854858A 1958-09-05 1958-09-05 Allo-ocimenol and its derivatives Expired GB875685A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2854858A GB875685A (en) 1958-09-05 1958-09-05 Allo-ocimenol and its derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2854858A GB875685A (en) 1958-09-05 1958-09-05 Allo-ocimenol and its derivatives

Publications (1)

Publication Number Publication Date
GB875685A true GB875685A (en) 1961-08-23

Family

ID=10277375

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2854858A Expired GB875685A (en) 1958-09-05 1958-09-05 Allo-ocimenol and its derivatives

Country Status (1)

Country Link
GB (1) GB875685A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012089301A1 (en) 2010-12-30 2012-07-05 Philip Morris Products S.A. Particle drying system and method

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012089301A1 (en) 2010-12-30 2012-07-05 Philip Morris Products S.A. Particle drying system and method

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