Reaction #1354137

Reaction equation

diketene

3,7-dimethyl-1,6-octadien-3-yl 3-(naphthyl)-3-oxo-propionate

3,7-dimethyl-1,6-octadien-3-ol

→

3,7-dimethyl-1,6-octadien-3-yl 3-oxo-butyrate

Conditions

Workup

1. 1
   Otheris prepared

Procedure

The pro-accord 3,7-dimethyl-1,6-octadien-3-yl 3-(naphthyl)-3-oxo-propionate, which is a β-ketoester pro-accord, is prepared by treating 3,7-dimethyl-1,6-octadien-3-ol (linalool), which is a fragrance raw material according to the present invention, with diketene under suitable conditions to form intermediate 3,7-dimethyl-1,6-octadien-3-yl 3-oxo-butyrate, which is subsequently treated with 2-naphthoyl chloride to yield the pro-accord. 3,7-Dimethyl-1,6-octadien-3-yl 3-(β-naphthyl)-3-oxo-propionate when exposed to suitable conditions (e.g., exposure to nascent moisture) breaks down to release a mixture of linalool and methyl β-naphthyl ketone, both of which are fragrance raw materials as defined herein.

Source