4-Hydroxybenzoic Acid → Benzoic acid, 4-(acetyloxy)-

Participants

Reaction Conditions

Reaction Steps

An amount of 4-hydroxybenzoic acid (92.1 g, 0.67 mole) was dissolved in a solution of sodium hydroxide (53.4 g, 1.33 moles) and 1.33 liters (L) of water in a 4 L beaker. The solution was stirred and cooled to a temperature of 0° C., then acetic anhydride (102.1 g, 1.00 mole) was added. The temperature was maintained at -2° C. for 1 hour. A solution of concentrated HCl (144.7 g, 1.42 mole) in 267 ml of water was added. The slurry was stirred briefly and filtered. The product was washed twice by stirring it with 2 L portions of fresh water then filtered and dried in a vacuum oven at 80° C. for 16 hours. After recrystallization from methyl isobutyl ketone, the product consisted of white crystals with a m.p. of 192° C. to 192.5° C.

Provenance & Evidence