GB807101A - Isomers of pseudoirones substituted at c, and/or c - Google Patents
Isomers of pseudoirones substituted at c, and/or cInfo
- Publication number
- GB807101A GB807101A GB6614/56A GB661456A GB807101A GB 807101 A GB807101 A GB 807101A GB 6614/56 A GB6614/56 A GB 6614/56A GB 661456 A GB661456 A GB 661456A GB 807101 A GB807101 A GB 807101A
- Authority
- GB
- United Kingdom
- Prior art keywords
- irones
- methyl
- mixture
- aceto
- dehydro
- 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
- 239000000203 mixture Substances 0.000 abstract 7
- 235000000396 iron Nutrition 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 238000006136 alcoholysis reaction Methods 0.000 abstract 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- -1 ethyl n-pentenoyl acetate Chemical compound 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Mixtures of stereo isomeric pseudo-irones substituted in the C9 and/or C11 positions are prepared from a mixture of dehydro-3-methyl linalool and an aceto-acetic ester having the general formula <FORM:0807101/IV (b)/1> wherein three at most of the radicals R1, R2, R3 and R4 may be hydrogen, the other or others being identical or different alkyl or alkenyl groups and R is the radical of an alcohol volatile under the rection conditions and capable of liberation by alcoholysis by the dehydro-3-methyl linalool, which comprises heating the mixture at a temperature at which simultaneous alcoholysis of the aceto acetic ester and the molecular rearrangement accompanied by decarboxylation of the ester resulting from the alcoholysis occur, the aceto acetic ester used being in such an excess that a substantially complete conversion of the dehydro-3-methyl linalool is ensured, and separating the mixture of pseudo-irones thereby formed from the other reaction products by distillation. The process allows 9-allyl and 11-allyl pseudo irones to be obtained in improved yield. The substituted pseudo-irones on cyclization yield the corresponding irones. In examples: (1) dehydro 3-methyl linalool and ethyl a -methyl aceto acetate (3 mols.) are heated together at 180 DEG C. and when evolution of CO2 and ethyl alcohol has ceased, the mixture is distilled under reduced pressure to remove excess aceto acetate and then a stereo isomeric mixture of 9-methyl pseudoirones which may be cyclised by the method of Specification 666,881 yielding a mixture of 22-methyl irones; (2) ethyl-a -n-propyl acetoacetate is reacted similarly yielding stereoisomeric 9-n-propyl pseudoirones which are cyclised by means of phosphoric acid to the 22-n-propyl irones; (3) ethyl n-pentenoyl acetate is reacted in the same manner yielding stereoisomeric 11-allyl pseudoirones which on cyclisation as in (1) are converted into 24-allyl irones. Specifications 762,656 and 803,364 also are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL807101X | 1955-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB807101A true GB807101A (en) | 1959-01-07 |
Family
ID=19836650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6614/56A Expired GB807101A (en) | 1955-03-10 | 1956-03-02 | Isomers of pseudoirones substituted at c, and/or c |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB807101A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5221797A (en) * | 1991-04-17 | 1993-06-22 | Rhone-Poulenc Nutrition Animale | Process for the purification of pseudo-ionone and a complex formed during said process |
-
1956
- 1956-03-02 GB GB6614/56A patent/GB807101A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5221797A (en) * | 1991-04-17 | 1993-06-22 | Rhone-Poulenc Nutrition Animale | Process for the purification of pseudo-ionone and a complex formed during said process |
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