Benzoic Acid → 4-Hydroxybenzoic Acid

Participants

Reaction Conditions

Reaction Steps

In this example 122.0 grams (1.0 moles) of benzoic acid are placed in a stainless steel autoclave containing 15.0 grams of benzonitrile and 500 grams of water containing 200.0 grams (5.0 moles) of sodium hydroxide. Thereafter, 12.0 grams of a 30 percent aqueous hydrogen peroxide solution is added to the autoclave during a period of time comprising 22 minutes. The autoclave is maintained at a temperature of 50°C and a pressure of one atmosphere during the entire 22 minutes of treatment time. At the end of the 22 minutes, the autoclave is allowed to return to room temperature and the treatment product transferred to a clean dry beaker. The treatment product is acidified, extracted with ether and the ether layer evaporated to produce a crude product. Fractional crystallization of the crude product in water and alcohol yields essentially pure 2-hydroxybenzoic acid, 3-hydroxybenzoic acid and 4-hydroxybenzoic acid.

Provenance & Evidence