GB813018A - A method for the preparation of isomeric tertiary alcohols - Google Patents
A method for the preparation of isomeric tertiary alcoholsInfo
- Publication number
- GB813018A GB813018A GB13685/57A GB1368557A GB813018A GB 813018 A GB813018 A GB 813018A GB 13685/57 A GB13685/57 A GB 13685/57A GB 1368557 A GB1368557 A GB 1368557A GB 813018 A GB813018 A GB 813018A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ionone
- dihydro
- per cent
- geranyl
- trimethyl
- 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
- C07C45/27—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
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
-
- 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
- C07C33/05—Alcohols containing rings other than six-membered aromatic rings
- C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Mixtures of the three isomeric 1,1,6-trimethyl - 6 - hydroxyoctahydronaphthalenes are prepared by cyclization of dihydro-g -ionone, itself formed in situ by treating dihydro-a -ionone with phosphoric acid containing pyridine (preferably 2-8 per cent by weight.) The dihydro-a -ionone may itself be produced in situ by using geranyl-acetone as the starting material. Another alcohol having the formula <FORM:0813018/IV (b)/1> is also produced in yields up to 20 per cent by direct cyclisation of dihydro-a -ionone, and is eliminated from the product of the reaction by distillation. In examples: (1) dihydro-a -ionone in benzene is added to cooled 84 per cent phosphonic acid containing pyridine, the mixture stirred under nitrogen, poured into water, extracted with petroleum ether and fractionated in vacuo; the alcoholic components are separated by treatment with ethyl borate, the borate compounds decomposed with KOH and the product again fractionated, giving a mixture of the three 1,1,6-trimethyl-6-hydroxy-octahydronaphthalenes; (2) as in (1), using a higher percentage of pyridine; (3) as in (1), employing geranyl-acetone as starting material.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH813018X | 1956-06-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB813018A true GB813018A (en) | 1959-05-06 |
Family
ID=4538685
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB13685/57A Expired GB813018A (en) | 1956-06-13 | 1957-04-30 | A method for the preparation of isomeric tertiary alcohols |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB813018A (en) |
-
1957
- 1957-04-30 GB GB13685/57A patent/GB813018A/en not_active Expired
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