Hydrochloric Acid → HCID 20039936, compound

Participants

Reaction Steps

A solution of 69 g (0.56 mol) of 4-methylaminophenol and 73.9 g (0.61 mol) of N,N-dimethylaniline in about 1.5 L of acetone was stirred mechanically under nitrogen in a 3 L flask. A solution of 119.6 g (0.56 mol) of 6-bromohexanoyl chloride in 100 mL of acetone was added as rapidly as the exotherm would allow at about 40° C. The reaction was refluxed for 2 hours on a steam bath, allowed to cool and poured into a solution of about 560 mL of 2N HCl in 2 L of ice. The aqueous solution was extracted twice with ethyl acetate and the ethyl acetate extracts were combined and dried over magnesium sulfate. The ethyl acetate solution was stripped to dryness under high vacuum to yield 143.4 g (85%) of greenish-white, low melting, solid 6-bromo-N-(4-hydroxyphenyl)-N-methylhexanamide.

Provenance & Evidence