2-(4-AMINO-3-NITROPHENOXY)ETHAN-1-OL synthesis

Yield:-

Reaction Conditions:

with potassium hydroxide;sodium chloride in N-methyl-acetamide;(2S)-N-methyl-1-phenylpropan-2-amine hydrate

Steps:

1 Preparation of (3-nitro 4-acetylamino)phenoxyethanol
Preparation of (3-nitro 4-acetylamino)phenoxyethanol 0.1 mole (19.6 g) of 3-nitro 4-acetylamino phenol is dissolved in 60 cc of dimethylformamide; there is then added to this solution 0.155 mole of 85% potassium hydroxide (10.2 g) in 22 cc of a dilute alcohol solution (20% water, 80% ethanol) and 0.17 mole (21.25 g) of glycol bromohydrin. At the end of two and a half hours of heating in a boiling double boiler, the reaction mixture is poured into 200 cc of ice water to which 70 g of sodium chloride are added to precipitate the (3-nitro 4-acetylamino)phenoxyethanol. The expected product is drained and dried under vacuum. After recrystallization in benzene and drying under vacuum it melts at 107° C.

References:

Societe Anonyme dite: L'OREAL US4337061, 1982, A