Acetic Anhydride → Isopropyl Acetate

Participants

Reaction Steps

A mixture of 3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (10.5 g.) (the starting material of part A of Example 1), acetic anhydride (25 ml.) and benzene (50 ml.) was heated under reflux for four hours, then concentrated. Methanol was added to the residue, and the mixture was boiled and concentrated. Excess saturated potassium carbonate solution was added to an aqueous solution of the residue, and the mixture was extracted with chloroform. The chloroform extract was dried, filtered and concentrated. Recrystallization of the residue first from ether, then from ether-acetone, then from isopropyl acetate afforded 4-acetyl-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (2.25 g., m.r. 105°-106° C.), the compound of Formula VIII.

Provenance & Evidence