Formaldehyde → 2-(Morpholin-4-ylmethyl)-5-ethylphenol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 244.0 grams (1.78 moles--1.0 equiv.) of 89.1% pure m-ethylphenol in 320 mL (%Wt/Vol. Phenol to Solvent--76.3%) of acetonitrile was added 67.6 grams (2.14 moles--1.2 equiv.) of paraformaldehyde. Upon completion of addition, the mixture was stirred for ten minutes and then heated to 65° C. where 179.5 grams (2.06 moles--1.16 equiv.) of morpholine was added during a one hour period at a rate to maintain the reaction temperature below 70-75° C. Upon completion of addition, the reaction mixture was heated to 70° C. where it stirred for two hours. At this point, the reaction mixture was analyzed by GC, which indicated that 2% of the phenol starting material remained. An additional 3.5 grams (0.04 mole--0.02 equiv.) of morpholine was added. Upon completion addition, the reaction mixture was stirred at 70° C. until GC analysis indicated that 1.1% of the phenol starting material remained. The acetonitrile was removed under vacuum, yielding 446.6 grams of 89.1% pure 2-(morpholin-4-ylmethyl)-5-ethylphenol (90% yield).

Provenance & Evidence