4-Hydroxybenzaldehyde → HCID 53767661, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (0.4 mole) was suspended in dimethyl formamide (20 ml). 4-Hydroxybenzaldehyde (0.2 mole) in DMF (50 ml) was added. After the effervesence had subsided, 2-chloropropanoic acid (0.22 mole) was added dropwise. During the addition the reaction temperature rose to 70° C. The mixture was stirred overnight at 110° C. Upon cooling the mixture was diluted with saturated NaHCO3 solution and extracted with ethyl acetate (3×100 ml). The aqueous phase was then acidified with concentrated HCl solution and extracted with ethyl acetate. After washing the second organic extract with water and evaporation, a brown oil was obtained. Crystallisation from hot chloroform and hexane gave a brown solid (7.6 g). The mother liquors were evaporated to dryness to yield a brown solid (17.3 g) used without further purification. (Total yield 64%). 'H-NMR spectroscopy showed these products to be greater than 90% pure (m.p. 114°-8° C.).

Provenance & Evidence