4-Amino-m-cresol → HCID 66704166, compound

Participants

Reaction Steps

4-Amino-m-cresol (242 g, 1.96 mol) is added to a slurry of 4-formyl-2-methyl-benzoic acid, methyl ester (350 g, 1.96 mol) and acetic acid (3100 mL) at room temperature. Sodium triacetoxyborohydride (728 g, 3.44 mol) is added portionwise, keeping the temperature below 30° C. using an ice water bath. After overnight stirring, the reaction mixture is concentrated under reduced pressure. The residue is adjusted to pH 5 using aqueous saturated sodium bicarbonate. The resulting solid is filtered off, washed with water, and dried under vacuum overnight to give the title compound (460 g, 82%) as a brown powder. ES/MS m/e 179 (M+1).

Provenance & Evidence