GB919454A - Ionone epoxide and the preparation of substituted ionones therefrom - Google Patents

Ionone epoxide and the preparation of substituted ionones therefrom

Info

Publication number
GB919454A
GB919454A GB3404559A GB3404559A GB919454A GB 919454 A GB919454 A GB 919454A GB 3404559 A GB3404559 A GB 3404559A GB 3404559 A GB3404559 A GB 3404559A GB 919454 A GB919454 A GB 919454A
Authority
GB
United Kingdom
Prior art keywords
ionones
acids
prepared
alkyl
keto
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
GB3404559A
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
Priority to GB3404559A priority Critical patent/GB919454A/en
Publication of GB919454A publication Critical patent/GB919454A/en
Expired legal-status Critical Current

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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
    • C07C45/298—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 with manganese derivatives

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)

Abstract

The invention comprises q -ionone epoxide of formula <F\1> which is prepared by the epoxidation under acid conditions of q -ionone with for example per-acids such as perbenzoic, monoperphthalic and peracetic acids. The reaction is carried out, preferably in solution in an inert solvent, such as ether or benzene, at a reduced temperature e.g. 0 DEG C. 6-hydroxyionones are prepared by cyclization with mineral or organic acids or Lewis acids to give b , or a - or g -isomers, which may be further oxidised with chromium trioxide to 6-keto derivatives, which may be further reacted with Grignard reagents after protecting the side chain Keto-group, to give 6-alkyl-6-hydroxy-ionones. 6-alkyl or 6aralkyl ionones may also be prepared from the epoxide by a process in which the keto-group is first reduced to hydroxyl, for example by sodium borohydride, or otherwise protected, by conversion to ketoxime or semicarbazone. The resulting epoxy-alcohol is reacted with Grignard reagents or lithium alkyl, oxidised with manganese dioxide or hydrolysed with dilute mineral acid (as appropriate) and finally cyclized by for example sulphuric, phosphoric, or toluene sulphonic acids and boron trifluoride, to the a -, b -, and g -ionones.
GB3404559A 1959-10-07 1959-10-07 Ionone epoxide and the preparation of substituted ionones therefrom Expired GB919454A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3404559A GB919454A (en) 1959-10-07 1959-10-07 Ionone epoxide and the preparation of substituted ionones therefrom

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3404559A GB919454A (en) 1959-10-07 1959-10-07 Ionone epoxide and the preparation of substituted ionones therefrom

Publications (1)

Publication Number Publication Date
GB919454A true GB919454A (en) 1963-02-27

Family

ID=10360680

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3404559A Expired GB919454A (en) 1959-10-07 1959-10-07 Ionone epoxide and the preparation of substituted ionones therefrom

Country Status (1)

Country Link
GB (1) GB919454A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110183321A (en) * 2019-04-25 2019-08-30 安徽中烟工业有限责任公司 A method of efficiently preparing keto-ionone
CN114014826A (en) * 2021-10-13 2022-02-08 上海应用技术大学 Preparation method of 6, 7-epoxy-gamma-ionone

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110183321A (en) * 2019-04-25 2019-08-30 安徽中烟工业有限责任公司 A method of efficiently preparing keto-ionone
CN110183321B (en) * 2019-04-25 2022-05-10 安徽中烟工业有限责任公司 Method for efficiently preparing oxoionone
CN114014826A (en) * 2021-10-13 2022-02-08 上海应用技术大学 Preparation method of 6, 7-epoxy-gamma-ionone

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