Acetic Anhydride → N-(4-cyclopentylphenyl)acetamide

Participants

Reaction Steps

To a solution of 1-cyclopentyl-4-nitrobenzene and 1-cyclopentyl-2-nitrobenzene (Preparation 96, 28.92 g, 151.2 mmol) in methanol (300 mL) was added acetic anhydride (20.1 mL, 213 mmol) and palladium (2 g, 20 mmol) (10% on carbon, Degussa type) and the reaction mixture hydrogenated at a pressure of 40 psi for 5 hours. The mixture was filtered through celite concentrated in vacuo, and purified by silica gel column chromatography eluting with a 0-50% ethyl acetate/hexanes gradient. The isomers separated at this stage to give (16.52 g, 54%) of product as a brown solid.

Provenance & Evidence