Benzene → methyl 3-[p-(epsilon-N-acetylaminocaproyl)phenyl]-propionate

Participants

Reaction Steps

Eight hundred milligrams of ε-N-acetylaminocaproyl chloride obtained by reacting ε-N-acetylaminocaproic acid with thionyl chloride in benzene was suspended in 20 ml of carbon disulfide. With vigorous stirring under ice cooling, 1.3 g of aluminum chloride was added. A solution of 550 mg of methyl phenylpropionate in 5 ml of carbon disulfide was added, and the mixture was stirred for 4 hours under reflux. After the reaction, the carbon disulfide layer was separated by decantation. A small amount of ice water was carefully added to the residue to decompose the excess of aluminum chloride. An aqueous solution of sodium hydroxide was added to the resulting aqueous solution to dissolve the resulting aluminum hydroxide. It was extracted three times with chloroform. The chloroform layer was washed with water and dried over anhydrous sodium sulfate. The chloroform was distilled off under reduced pressure to give 900 mg of a white oily substance. The product had the following NMR spectrum and identified as the title compound.

Provenance & Evidence