Abstract
The compound obtained from the reaction of 2-hydroxybenzylamine (1) with equimolar amount of formaldehyd, previously reported as 3, 4-dihydro-2H, 1, 3-benzoxazine was identified in the present paper to be 1, 3, 5-tris (2-hydroxybenzyl) -hexahydro-s-triazine (2) in agreement with McDonagh's report.
It was also found that the reaction of (1) with double the molar quantity of formaldehyde gave 3, 3′-methylene-bis (3, 4-dihydro-2H, 1, 3-benzoxazine) (3) as reported by Holly and that the mutual relation among (1), (2), (3), and the reaction products of (2) or (3) with excess phenol summerized as follows :
The effect of substituents, H, CH3, and Cl in the position of (1), was not observed within the scope of this experiment.
