Sulfuric Acid → (3-(Phenylamino)phenyl)methanol

Participants

Reaction Steps

Under cooling with ice water, 7.2 g of sodium borohydride was gradually dropped into 4.5 g of methyl 3-anilinobenzoate dissolved in 20 ml of methanol. Then, the temperature was gradually raised and the reflux was carried out for 8 hours. The reaction mixture was poured into 10% H2SO4 aqueous solution which was being cooled with ice. 5.0 g of oily substance was obtained after the extraction with ether. In order to remove the remaining unreacted methyl ester, the hydrolysis was carried out with the addition of 5% KOH. The by-produced 3-anilinobenzoic acid was removed through alkali-washing to yield 3.5 g of 3-anilinobenzylalcohol.

Provenance & Evidence