Diethyl Succinate → HCID 14742750, compound

Participants

Reaction Steps

As in Example 130, 1-phenylpentanone (50 g) was reacted with diethyl succinate (80.5 g) in t-butanol at 60° C. for 6 hours in the presence of potassium t-butoxide (38 g). The normal work up furnished 81 g of a mixture of the isomeric 3-(ethoxycarbonyl)-3-octenoic acids as an oil. The acids (79.4 g) were cyclized as before by refluxing in acetic anhydride (500 mL) containing sodium acetate (22.5 g) for 9 hours. After work up, the crude product was passed through a short column of silica gel (650 g) made up in dichloromethane-hexane (2:1) to give 60 g of 4-acetoxy-1-butyl-2-naphthalenecarboxylic acid ethyl ester as an oil.

Provenance & Evidence