3-Hydroxybenzaldehyde → 3-(Morpholinomethyl)phenol

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Reaction Steps

To a solution of 0.2 mol of 3-hydroxybenzaldehyde in 100 ml of methanol, is added, at about 20° C., a solution of 0.4 mol of morpholine in 40 ml of methanol. To the mixture thus obtained is added portionwise, under stirring at the temperature of 20°-25° C. within about 90 minutes, 0.2 mol of sodium borohydride, then the reaction mixture is stirred 3 hours at room temperature and the solvent is evaporated under reduced pressure to dryness. The residue is taken up with ice and acidified with hydrochloric acid, the acid solution is washed twice with 40 ml of ethyl acetate and concentrated ammonium hydroxide is added thereto up to clearly basic reaction. The mixture is extracted 4 times with 80 ml of ethyl acetate and the solvent is evaporated off. The product thus obtained melts at 113°-116° C. Yield: 67%.

Provenance & Evidence