Ethyl chloroformate → 2-[4-(4-Chlorophenoxy)-phenoxy]-propanol

Participants

Reaction Conditions

Reaction Steps

13.8 ml. of triethylamine are added, at 10° C., to a solution of 29.25 g. of 2-[4-(4-chlorophenoxy)-phenoxy]-propionic acid in 200 ml. of THF. The mixture is cooled to -10° C., a solution of 9.8 ml. of chloroformic acid ethyl ester in 60 ml, of THF is added dropwise and the mixture is stirred for 1 hour at -10° C. The solution contains 1-[4-(4-chlorophenoxy)-phenoxy]-4,6-dioxa-octane-3,5-dione, which is not isolated. 7.4 g. of NaBH4 are then introduced in portions. The mixture is stirred for 30 minutes at -10° C. and for 30 minutes at 0° C., poured into water and extracted with chloroform. After evaporation of the extract, the residue is boiled for 1 hour with 200 ml. of 6% ethanolic potassium hydroxide solution, the mixture is evaporated and worked up with water and ether to give 2-[4-(4-chlorophenoxy)-phenoxy]-propanol.

Provenance & Evidence