GB789247A - Novel unsaturated alcohols and a process for the manufacture thereof - Google Patents
Novel unsaturated alcohols and a process for the manufacture thereofInfo
- Publication number
- GB789247A GB789247A GB26402/55A GB2640255A GB789247A GB 789247 A GB789247 A GB 789247A GB 26402/55 A GB26402/55 A GB 26402/55A GB 2640255 A GB2640255 A GB 2640255A GB 789247 A GB789247 A GB 789247A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trimethyl
- dimethyl
- dodecadien
- undecen
- reacting
- 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- 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
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 3, 7, 10, 11-tetra-methyl-dodecatrien-(1,6,10)-ol-3 and 3,7,11-trimethyl-dodecadien-(1,6)-ol-3 and their manufacture by reacting a metal derivative of acetylene with 6,9,10 - trimethyl - undecadien-(5,9)-one-2 or 6,10-dimethyl-undecen-(5)-one-2 respectively, hydrolysing the resulting acetylenic alcoholate and partially hydrogenating the liberated acetylenic carbinol at the triple bond in the presence of a hydrogenation catalyst which selectively catalyses the reduction of a triple bond to a double bond. In Examples: (1) an ethereal solution of 6,9,10-trimethyl-undecadien-(5,9)-one-2 is added dropwise to a liquid ammonia solution of sodium acetylide under a slight pressure of acetylene; the product is stripped of ammonia, treated with dilute aqueous sulphuric acid and the liberated 3,7,10,11 - tetramethyl - dodecadien - (6,10) - yn-(1)-ol-3 is recovered and partially hydrogenated in petroleum ether solution using a Lindlar lead-deactivated palladium catalyst and the resulting trien-ol is isolated from the product; (2) in like manner 6,10-dimethyl-undecen-5-one-2 is converted via 3,7,11-trimethyl - dodecen - (6) - yn - (1) - ol - 3 into 3,7,11 - trimethyl - dodecadien - (1,6) - ol - 3. The two polyolefinic carbinols and the intermediate acetylenic carbinol of (2) are useful in the preparation of perfumes. 6,10 - Dimethyl - undecen - 5 - one - 2 may be prepared as described in Specification 788,301 or by reacting 3,7-dimethyl-octen-(1)-ol-3 with concentrated hydrochloric acid to form 1-chloro-3,7 - dimethyl - octene - 2 (see Specification 735,828), then reacting the chloro-compound with the sodium salt of ethyl acetoacetate in benzene and subjecting the resulting product to hydrolysis and decarboxylation by means of aqueous caustic potash and then concentrated hydrochloric acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US789247XA | 1954-09-15 | 1954-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB789247A true GB789247A (en) | 1958-01-15 |
Family
ID=22147051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26402/55A Expired GB789247A (en) | 1954-09-15 | 1955-09-15 | Novel unsaturated alcohols and a process for the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB789247A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292454A (en) | 1977-12-29 | 1981-09-29 | Scm Corporation | Coupling reaction involving a Grignard and allylic halide |
-
1955
- 1955-09-15 GB GB26402/55A patent/GB789247A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292454A (en) | 1977-12-29 | 1981-09-29 | Scm Corporation | Coupling reaction involving a Grignard and allylic halide |
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