Carbonylation of allylic alcohols and synthesis of an ambergris fragance compound
AssigneeHenkel Research Corporation
InventorsJonathan M. Cassel, Steven M. Hoagland, James M. Renga
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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.
Claims10
A process for the preparation of an ambergris fragrance compound having the structure (B) ##STR7## comprising carbonylating an allylic alcohol selected from the group consisting of nerolidol, monocyclonerolidol, farnesol, and monocyclofarnesol with carbon monoxide at a pressure of at least about 30 bar in the presence of a polar solvent and an effective amount of a palladium halide catalyst;
- reducing the carbonylated product, either as the acid form or as the ester, to homofarnesol or monocyclohomofarnesol;
- and treating the reduced product under acid-catalyzed conditions to undergo cyclization.
Dependencies are inferred from the claim text.