Carbonylation of allylic alcohols and synthesis of an ambergris

Details Carbonylation of allylic alcohols and synthesis of an ambergris Carbonylation of allylic alcohols and synthesis of an ambergris

1994-03-23

1997-06-17

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

560 8, 560101, 560104, 560114, 560207, 562406, 562491, 562495, 562498, 562500, 562519, C07D30792, C07C 5112, C07C 6976, C07C 6736

Patent

active

056398948

ABSTRACT:
A process for the carbonylation of allylic alcohols such as nerolidol, farnesol, or their monocyclic analogues with carbon monoxide at a pressure of at least 30 bar in the presence of a polar solvent and a palladium halide catalyst, optionally an alkali metal halide salt, and optionally an alcoholic solvent. The carbonylated product may then be reduced to the corresponding alcohol, which is cyclized in the presence of Lewis or Bronsted acids to afford an ambergris fragrance compound.

REFERENCES:
patent: 3655745 (1972-04-01), Fenton
patent: 4189608 (1980-02-01), Kurkov
patent: 4585594 (1986-04-01), Himmele et al.
patent: 5326888 (1994-07-01), Cassel et al.
Chemical Abstract vol. 112, No. 178087, Alper, (1989), "Preparation of unsaturated carboxylic acids by carbonylation of allylic alcohols".

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