GB883228A - Manufacture of oct-3,5-dien-2,7-dione and oct-4-en-2,7-dione from oct-7-ol-3,5-dien-1-yne - Google Patents
Manufacture of oct-3,5-dien-2,7-dione and oct-4-en-2,7-dione from oct-7-ol-3,5-dien-1-yneInfo
- Publication number
- GB883228A GB883228A GB11907/58A GB1190758A GB883228A GB 883228 A GB883228 A GB 883228A GB 11907/58 A GB11907/58 A GB 11907/58A GB 1190758 A GB1190758 A GB 1190758A GB 883228 A GB883228 A GB 883228A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oct
- dien
- dione
- yne
- effected
- 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
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
- C07C45/26—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydration of carbon-to-carbon triple bonds
Abstract
Oct-3,5-dien-2,7-dione is prepared by oxidising oct-7-ol-3,5-dien-1-yne to oct-7-one-3,5-dien-1-yne and hydrating the latter to form the desired dienic dione or by hydrating the oct-7-ol-3,5-diene-1-yne to oct-7-ol-3,5-dien-2-one and oxidising the latter to the dienic dione. Both oxidations of the >CH.OH group to a carbonyl group may be effected with a slurry of manganese dioxide in an inert organic solvent; with tertiary butyl chromate; or with an aluminium tertiary alkoxide in the presence of a hydrogen acceptor. The hydrations of the acetylenic bond to form a carbonyl group may be effected in an aqueous methanol or acetone or other aqueous solvent system which may contain a hydration catalyst such as sulphuric, phosphoric or formic acid in combination with a mercury compound such as mercuric oxide or p sulphate, or which may contain perchloric acid or BF3, alone or with a mercury compound. The resulting oct-dienic dione may be converted into oct-4-en-2,7-dione by partial hydrogenation by treatment, for example, with a metal-acid combination such as zinc and acetic acid, in an amine solvent such as pyridine. The oct-7-ol-3,5-dien-1-yne starting material may be prepared by ethylynating sorbaldehyde and subjecting the resulting oct-4,6-dien-3-ol-1-yne to an alkylic rearrangement. The ethylynation may be effected by reacting the sorbaldehyde with a Grignard reactant CHC.MgX or with the acetylide of a basic metal such as lithium, sodium, potassium or calcium, if desired in a solvent, and hydrolysing the resulting complex, e.g. with aqueous brine or NH4Cl solution. The basic metal acetylide may be preformed or may be formed in situ by using liquid ammonia as a solvent and adding the metal and then acetylene thereto. The alkylic rearrangement may be effected by treating with an aqueous solution of sulphuric, hydrochloric, phosphoric, formic, acetic, trichloracetic or other acid, preferably in the presence of an anti-oxidant such as hydroquinone, butylated hydroxy anisole or butylated hydroxytoluene, under an inert atmosphere. Examples describe the synthesis of oct-4-en-2,7-dione from sorbaldehyde by both multi-stage processes described above, the intermediates being isolated and purified after each stage.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US883228XA | 1957-04-17 | 1957-04-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB883228A true GB883228A (en) | 1961-11-29 |
Family
ID=22210694
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB11907/58A Expired GB883228A (en) | 1957-04-17 | 1958-04-15 | Manufacture of oct-3,5-dien-2,7-dione and oct-4-en-2,7-dione from oct-7-ol-3,5-dien-1-yne |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB883228A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1233001A3 (en) * | 2001-02-16 | 2004-03-03 | Tosoh Corporation | Lithium-manganese complex oxide, production method thereof and use thereof |
-
1958
- 1958-04-15 GB GB11907/58A patent/GB883228A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1233001A3 (en) * | 2001-02-16 | 2004-03-03 | Tosoh Corporation | Lithium-manganese complex oxide, production method thereof and use thereof |
US6814894B2 (en) | 2001-02-16 | 2004-11-09 | Tosoh Corporation | Lithium-manganese complex oxide, production method thereof and use thereof |
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