GB828591A - Novel bicyclic compounds and a process for the manufacture thereof - Google Patents
Novel bicyclic compounds and a process for the manufacture thereofInfo
- Publication number
- GB828591A GB828591A GB16299/58A GB1629958A GB828591A GB 828591 A GB828591 A GB 828591A GB 16299/58 A GB16299/58 A GB 16299/58A GB 1629958 A GB1629958 A GB 1629958A GB 828591 A GB828591 A GB 828591A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alcohol
- ketone
- type
- acid
- saturated
- 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
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
- C11B9/0053—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms both rings being six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 1-hydroxy-naphthalenes of the formul <FORM:0828591/IV (b)/1> <FORM:0828591/IV (b)/2> and esters thereof and 1-keto-naphthalenes of the formul <FORM:0828591/IV (b)/3> <FORM:0828591/IV (b)/4> <FORM:0828591/IV (b)/5> where R1, R2 and R3 represent optional alkyl groups containing up to six carbon atoms (the broken lines denoting the optional bonds thereto). The preferred compounds are those in which R1, R2 and R3 are absent, i.e. the 2,5,5,9 - tetramethyl substituted compounds. The compounds may be prepared by a process which comprises or includes as a first step treating an aldehyde of the formula <FORM:0828591/IV (b)/6> with an acidic agent to give the unsaturated alcohol I. The alcohol I may then be treated by methods known per se for the purposes of esterification, isomerization, hydrogenation of the double bond or oxidation of the hydroxyl group and one or more such operations may be carried out in any order. The cyclization of the aldehyde preferably takes place in the presence of phosphoric acid and in the absence of any solvents, the acidic agent may, however, be formic or acetic acid in which case the appropriate ester of alcohol I is directly obtained. Esterification of the alcohols may be carried out using acid halides or anhydrides in the presence of pyridine, hydrogenation of the double bond catalytically in the presence of palladium, oxidation of the hydroxy group with chromic acid in acetic acid, isomerization at the double bond of the unsaturated ketone by means of sulphuric acid and isomerization of the alcohol at the hydroxy group by oxidizing it to a keto group and then reducing the ketone with lithium aluminium hydride. In the examples: (1) 4 - [21,61,61 - trimethyl - cyclo - hexen - 11 - yl] - 2 - methyl - butanal - 1 is cyclized to give 2,5,5,9 - tetramethyl - 1 - hydroxy - 1,2,3,5,6,7,8,9-octahydronaphthalene and its esters are prepared with formic, acetic and benzoic acids; the unsaturated alcohol is reduced to the corresponding saturated alcohol (type II) which is in turn oxidized to the saturated ketone (type V), hydride reduction of this ketone gives a saturated alcohol isomeric with the one mentioned above; the unsaturated alcohol (type I) is oxidized to the ketone (type III) which is isomerized to ketone (type IV) and then reduced to a saturated ketone (type V) which is isomeric with the one mentioned above; (2) and (3) the formate and acetate esters of the unsaturated alcohol (type I) above are directly prepared by cyclizing the aldehyde in the presence of formic and acetic acids.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH828591X | 1957-05-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB828591A true GB828591A (en) | 1960-02-17 |
Family
ID=4540132
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB16299/58A Expired GB828591A (en) | 1957-05-21 | 1958-05-21 | Novel bicyclic compounds and a process for the manufacture thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB828591A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0047154A2 (en) * | 1980-08-29 | 1982-03-10 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Methyl-substituted oxy- and oxo-bicyclo-4,4,0-decane derivatives, process for preparing the same and organoleptic uses thereof |
-
1958
- 1958-05-21 GB GB16299/58A patent/GB828591A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0047154A2 (en) * | 1980-08-29 | 1982-03-10 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Methyl-substituted oxy- and oxo-bicyclo-4,4,0-decane derivatives, process for preparing the same and organoleptic uses thereof |
EP0047154A3 (en) * | 1980-08-29 | 1982-08-11 | International Flavors & Fragrances Inc. | Methyl-substituted oxy- and oxo-bicyclo-4,4,0-decane derivatives, process for preparing the same and organoleptic uses thereof |
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