4-hydroxy-N-(3-hydroxypropyl)benzamide → 4-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol

Participants

Reaction Steps

A mixture of 37.8 g of N-(3-hydroxypropyl)-4-hydroxybenzamide and 100 ml of thionyl chloride was stirred for 1.5 hours. The reaction mixture was concentrated in vacuo, the solid residue triturated with ethyl acetate, and converted to the free base by treatment with ammonium hydroxide. There was obtained 10.2 g of 4-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol, m.p. 196°-198° C. (from methanol).

Provenance & Evidence