Acetic Anhydride → HCID 20039927, compound

Participants

Reaction Steps

A solution of 4 g (0.017 mol) of 7-[(4-hydroxyphenyl)methylamino]heptanenitrile and 2.1 g (0.026 mol) anhydrous sodium acetate in 14 mL (0.17 mol) of acetic anhydride was stirred under nitrogen at room temperature. After 11/2 hours 15 mL of ethyl acetate was added followed by 49 mL of absolute ethanol. The reaction was stirred 18 hours at room temperature, cooled, and 61 mL of water was added followed by about 11 g of solid potassium bicarbonate. The layers were separated and the aqueous layer was extracted twice with ethyl acetate. The ethyl acetate extracts were combined, washed three times with saturated sodium bicarbonate solution, two times with saturated sodium chloride solution, and dried over magnesium sulfate. The solution was concentrated in vacuo to 3.4 gm of amber oil which was distilled at 170°-172°/0.08 mm in a Kugelrohr to yield 2.7 g (59%) of 7-[[4-(acetyloxy)phenyl]methylamino]heptanenitrile.

Provenance & Evidence