Thionyl Chloride → Ethyl 12-(acetyloxy)-8-(chlorocarbonyl)heptadecanoate

Participants

Reaction Steps

A solution of ethyl 8-carboxy-12-acetoxyheptadecanoate (12.0 g., 0.03 mole) and thionyl chloride (7.2 g., 0.06 mole) in benzene (50 ml.) is refluxed for 2.5 hours. Volatile materials are removed by using a rotary evaporator in vacuo. The residual product, ethyl 8-chlorocarbonyl-12-acetoxyheptadecanoate, is a viscous liquid weighing 12.5 g. (100%), ir (neat) 1790 cm-1 (acid chloride C=O), 1730 cm-1 (ester C=O). This material is used directly in the next step.

Provenance & Evidence