Potassium Hydroxide → Acetic acid, (3-pentadecylphenoxy)-

Participants

Reaction Steps

A 2-L round bottom flask equipped with a magnetic stirring bar and a reflux condenser was charged with potassium hydroxide (28 g, 0.5 mol) and methanol (1-L). To this vigorously stirred mixture, methyl (3-pentadecylphenoxy)acetate (93 g, 0.247 mol) was added and the resulting slurry was brought to a gentle reflux (2 hr). The ester was not completely soluble. The reaction was monitored by TLC. The hydrolysis was complete in 2 hr. The mixture was cooled and poured into crushed ice-water-hydrochloric acid mixture to precipitate the acid as white solid. The acid was dried and further purified by trituration from hot methanol to afford 82 g (92% yield) of the acid, mp 96° C.

Provenance & Evidence