Dimethylamine → 2-((Dimethylamino)methyl)phenol

Participants

Reaction Steps

2-Dimethylaminomethyl phenol was prepared by the method of S. Cavitt, "J. Org. Chem.", 27, 1211 (1962). 61.0 gm salicylaldehyde, 127 gm 25% by wt dimethylamine in water and 1.2 gm 10% by wt palladium on charcoal are placed in a pressure bottle of a Parr hydrogenator and hydrogenated until 41.7 lbs of hydrogen are taken up. The experiment is repeated and reaction mixtures combined. The catalyst is filtered off and the filtrate made acidic (pH 2), extracted with ether, and the ether discarded. The aqueous phase is adjusted to pH 8 with NaOH and extracted with ether. The aqueous phase is adjusted to pH 9 with NaOH and extracted with ether. The ether extracts are combined, dried over MgSO4, filtered, and evaporated on a rotating evaporator. There results 111.7 gm of an orange liquid (Percent crude yield - 75). This is fractionated at reduced pressure. The product is collected at 60°-63° C. at 0.5 mm to provide 99.1 gm of a yellow liquid (Percent yield - 65).

Provenance & Evidence