Hydrochloric Acid → 5-[4-(Hydroxymethyl)phenyl]imidazolidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of p-hydroxymethylbenzaldehyde (10.0 g., 0.0735 mole) and ammonium carbonate (17.1 g., 0.15 mole) in 110 ml. of 60% ethanol heated to 50° C. there was added dropwise sodium cyanide (4.0 g., 0.081 mole) dissolved in 10 ml. water. The mixture was stirred and heated to 55°-60° C. for three hours and then the temperature raised to 85° C. for one hour. After cooling in an ice bath, the pH of the solution was brought to 6 by the addition of concentrated hydrochloric acid. Upon overnight cooling, the solid which had precipitated was filtered, washed with cold water, and dried. The 5-(p-hydroxymethylphenyl)hydantoin (11.0 g., 72% yield), m.p. 189°-196° (dec.), was used to prepare the amino acid without further purification.

Provenance & Evidence