3-Hydroxybenzaldehyde → 3-(Morpholinomethyl)phenol

Participants

Reaction Steps

To a solution of 15 g. (0.123 mole) of 3-hydroxybenzaldehyde in 150 ml of ethanol is added 26.5 g (0.304 mole) of morpholine. Then 4.7 g (0.124 mole) of sodium borohydride is added portionwise over 1 hour. The solution is stirred for 1 hour and allowed to sit overnight. The solvent is then evaporated via a rotary evaporator and the residue triturated with 200 ml cold water. After acidification with concentrated HCl, the solution is extracted with ethyl acetate. The aqueous layer is basified with ammonium hydroxide and extracted again with 100 ml ethyl acetate. The organic layer is dried over MgSO4, filtered and evaporated. The residue is recrystallized twice from acetonitrile to give 6.3 g of product m.p. 113°-15° C.

Provenance & Evidence