Phenol → 3-Phenoxypropionic acid

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Reaction Steps

Phenol (203 g, 2.16 moles) is added to a solution of potassium hydroxide (112 g, 2.0 mole) in water (100 ml) at 70° C. The resulting solution is maintained at a temperature of 70° C and small portions of 3-chloropropionic acid (101 g, 0.93 mole) in water (100 ml) and potassium hydroxide (44 g, 0.81 mole) in water (50 ml) are added alternately over a period of 0.5 hour. The reaction solution is heated at reflux temperature for 10 min., cooled to room temperature and washed with ether. The aqueous phase is acidified with hydrochloric acid and extracted with ether. The combined ethereal extracts are shaken with sodium carbonate solution. The aqueous part is acidified with hydrochloric acid and extracted with ether. The combined organic extracts are dried, evaporated and crystallized from ether-petroleum ether to give the title compound, m.p. 95°-97° C [lit. m.p. 97°-98° C as reported by S. G. Powell, J. Amer. Chem. Soc., 45, 2711 (1923)].

Provenance & Evidence