Formaldehyde → 3-(beta-Hydroxypropyl)tetrahydro-1,3-oxazine
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6]CCO.C=[O:11].[C:12]1([CH3:18])[CH:17]=CC=CC=1>>[OH:11][CH:12]([CH3:18])[CH2:17][N:5]1[CH2:4][CH2:3][CH2:2][O:1][CH2:6]1Participants
4
Conditions
- Temperature
- 90 °C
Procedure
To a glass reaction vessel equipped with stirrer, thermometer, and condenser fitted with a water trap is added di-(3-hydroxypropyl) amine (3.0 mole, 399 g.) and toluene (500 g.). Paraformaldehyde (3.15 mole, 90% pure, 105 g.) is weighed out and about 1/3 is added to the amine solution. The resulting mixture is stirred and heated to 90° C. while slowly adding the remaining paraformaldehyde in about 70 minutes. The reaction is heated to reflux and the water separated. After 4 hours, a total of 63 ml. of water is removed. Toluene is removed at reduced pressure. The residue is distilled at high vacuum to yield 3-(β-hydroxypropyl)tetrahydro-1,3-oxazine.