GB646962A - Improvements in or relating to processes for the preparation of farnesylacetone - Google Patents
Improvements in or relating to processes for the preparation of farnesylacetoneInfo
- Publication number
- GB646962A GB646962A GB343348A GB343348A GB646962A GB 646962 A GB646962 A GB 646962A GB 343348 A GB343348 A GB 343348A GB 343348 A GB343348 A GB 343348A GB 646962 A GB646962 A GB 646962A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nerolidyl
- nerolidol
- acetoacetate
- trimethyl
- farnesylacetone
- 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
- LTUMRKDLVGQMJU-UHFFFAOYSA-N famesylacetone Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=O LTUMRKDLVGQMJU-UHFFFAOYSA-N 0.000 title abstract 4
- LTUMRKDLVGQMJU-IUBLYSDUSA-N farnesyl acetone Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)=O LTUMRKDLVGQMJU-IUBLYSDUSA-N 0.000 title abstract 4
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 abstract 3
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 abstract 3
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 abstract 3
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- -1 aliphatic ester Chemical class 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 abstract 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 238000000197 pyrolysis Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 150000007659 semicarbazones Chemical class 0.000 abstract 1
- 150000003385 sodium Chemical class 0.000 abstract 1
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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Farnesylacetone (2 : 6 : 10 - trimethyl - penta-decatriene-1 (or 2) : 6 : 10-one-14) is obtained as a mixture of stereoisomers by converting nerolidol into nerolidyl acetoacetate and pyrolysing the latter; the nerolidyl acetoacetate is obtained from nerolidol either by treating it with diketene, preferably in the presence of the sodium derivative of nerolidol, or by the action of a lower aliphatic ester of acetoacetic acid (e.g. methyl, ethyl) in the presence of an alcohol exchange catalyst such as potassium carbonate. In the latter case, the nerolidyl acetoacetate may be converted into farnesyl acetone without being isolated, the reaction mixture being merely heated. The pyrolysis may be effected in the presence or absence of an alkaline catalyst. Farnesyl acetone may be catalytically hydrogenated to 2 : 6 : 10 - trimethyl - pentadecanol-14 and this converted into 2 : 6 : 10-trimethyl-pentadecanone-14 by catalytic dehydrogenation or by oxidation, e.g. with chromic acid. The semicarbazone of the saturated ketone is described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH260081T | 1947-02-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB646962A true GB646962A (en) | 1950-11-29 |
Family
ID=4473339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB343348A Expired GB646962A (en) | 1947-02-18 | 1948-02-05 | Improvements in or relating to processes for the preparation of farnesylacetone |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH260081A (en) |
| FR (1) | FR1013483A (en) |
| GB (1) | GB646962A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2660608A (en) * | 1953-11-24 | Ent office | ||
| US2662920A (en) * | 1952-06-10 | 1953-12-15 | Hoffmann La Roche | Process for preparing 2, 3-dimethylheptene-2-one-6 |
| US2766289A (en) * | 1956-10-09 | Process for the production of | ||
| DE1046029B (en) * | 1955-08-24 | 1958-12-11 | Hoffmann La Roche | Process for the production of new unsaturated ketones with special fragrance properties |
| US3023246A (en) * | 1962-02-27 | Production of branched unsaturated |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870210A (en) * | 1954-12-07 | 1959-01-20 | Hoffmann La Roche | 6, 10, 12-trimethyl-5, 9-tridecadien-2-one |
| DE1026743B (en) * | 1955-03-31 | 1958-03-27 | Basf Ag | Process for the production of unsaturated ketones |
-
1947
- 1947-02-02 FR FR1013483D patent/FR1013483A/en not_active Expired
- 1947-02-18 CH CH260081D patent/CH260081A/en unknown
-
1948
- 1948-02-05 GB GB343348A patent/GB646962A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2660608A (en) * | 1953-11-24 | Ent office | ||
| US2766289A (en) * | 1956-10-09 | Process for the production of | ||
| US3023246A (en) * | 1962-02-27 | Production of branched unsaturated | ||
| US2662920A (en) * | 1952-06-10 | 1953-12-15 | Hoffmann La Roche | Process for preparing 2, 3-dimethylheptene-2-one-6 |
| DE1046029B (en) * | 1955-08-24 | 1958-12-11 | Hoffmann La Roche | Process for the production of new unsaturated ketones with special fragrance properties |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1013483A (en) | 1952-07-29 |
| CH260081A (en) | 1949-02-28 |
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