Hydrochloric Acid → 6-Acrylamidohexanoic Acid

Participants

Reaction Steps

To a solution of 6-Aminocaproic acid (10.0 g) in a 1.27 M aqueous sodium hydroxide solution (60 ml) was added a solution of acryloyl chloride (7.8 ml) in tetrahydrofuran (20 ml) dropwisely while chilling in ice water. During the addition, the reaction mixture was adjusted to be pH 8 to 9 by addition of 4 N aqueous sodium hydroxide solution. After the addition, the resulting mixture was stirred for 2 hours while being gradually cooled to room temperature. Subsequently, the reaction mixture was adjusted to be pH 3 by addition of 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with distilled water and dried over anhydrous magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in a small amount of ethyl acetate and recrystallized from hexane to give the target compound (9.6 g).

Provenance & Evidence