Ethanol → Hydroxyphenylacetic acid

Participants

Reaction Steps

At first, 1,200 ml of ethanol and 400 ml of water were added to 428 g (1.18 moles) of the compound (d) in a nitrogen atmosphere to prepare a homogeneous solution. Then, 101 g (1.45 moles) of hydroxylamine hydrochloride and 373 g (2.74 moles) of sodium acetate trihydrate were added thereto, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure to about 1,000 ml, and extracted with ethyl ether (3×300 ml). The ethyl ether layer was washed successively with an aqueous 5% sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution (each 2×100 ml), and dried over anhydrous sodium sulfate. The solvent was removed therefrom under reduced pressure to obtain 441 g of the compound (a) as an orange oily substance (99.1%).

Provenance & Evidence