GB989045A - Process for the preparation of compounds of the ionone series - Google Patents
Process for the preparation of compounds of the ionone seriesInfo
- Publication number
- GB989045A GB989045A GB1323863A GB1323863A GB989045A GB 989045 A GB989045 A GB 989045A GB 1323863 A GB1323863 A GB 1323863A GB 1323863 A GB1323863 A GB 1323863A GB 989045 A GB989045 A GB 989045A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trans
- compounds
- addends
- ionone
- pseudoionone
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 229930002839 ionone Natural products 0.000 title abstract 2
- 150000002499 ionone derivatives Chemical class 0.000 title abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 150000007530 organic bases Chemical class 0.000 abstract 2
- 239000000370 acceptor Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000000872 buffer Substances 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- -1 carboxylic acids Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 125000001477 organic nitrogen group Chemical group 0.000 abstract 1
- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 239000007974 sodium acetate buffer Substances 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
g -Compounds of the ionone series are made by cyclizing pseudoionone and its homologues in the presence of BF3 complex compounds, the addends of which are formed by compounds which are not subject to the cyclization reaction, e.g. water, alcohols, esters, carboxylic anhydrides, carboxylic acid esters, ketones, dialkyl sulphides and sulphoxides, and particularly ethers. The polar addends may be used in an excess over the amount necessary for the formation of the BF3 complex. Proton acceptors such as organic bases, particularly organic nitrogen-containing bases, including dimethyl formamide and pyridine, may also be added. A preferred embodiment involves the use of free acids, e.g. carboxylic acids, as polar addends together with organic bases or inorganic buffer systems. Thus a compound of BF3 and acetic acid with a sodium acetate buffer may be used as the catalyst. Prefererd temperatures are within the range - 10 DEG C. and + 40 DEG C., particulary between 25 DEG and 30 DEG C. Examples describe the conversion of trans-pseudoionone to g -ionone; trans-pseudoirone to g -irone; trans-pseudo-n-methylionone to g -n-methylionone; trans-pseudo-isomethylionone to g -isomethylionone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEST19085A DE1283835B (en) | 1962-04-12 | 1962-04-12 | Process for the preparation of ª † compounds of the Jonon series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB989045A true GB989045A (en) | 1965-04-14 |
Family
ID=7458089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1323863A Expired GB989045A (en) | 1962-04-12 | 1963-04-03 | Process for the preparation of compounds of the ionone series |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH465594A (en) |
| DE (1) | DE1283835B (en) |
| GB (1) | GB989045A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3328440A1 (en) * | 1983-08-06 | 1985-02-21 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING JONONS |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1030827B (en) * | 1956-02-23 | 1958-05-29 | Hoffmann La Roche | Process for the preparation of 4- [3-AEthyl-2, 6, 6-trimethyl-cyclohexen- (2) -yl] -butene- (3) -one- (2) |
| DE1112736B (en) * | 1959-01-16 | 1961-08-17 | Hoffmann La Roche | Process for the production of alicyclic ketones with valuable fragrance properties |
-
1962
- 1962-04-12 DE DEST19085A patent/DE1283835B/en active Pending
-
1963
- 1963-04-02 CH CH414463A patent/CH465594A/en unknown
- 1963-04-03 GB GB1323863A patent/GB989045A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1283835B (en) | 1968-11-28 |
| CH465594A (en) | 1968-11-30 |
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