Hydrochloric Acid → 2-(4-tert-butylphenoxy)propanoic acid

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Reaction Steps

To a chilled slurry of 9.3 g of sodium hydride-oil dispersion (57%) in 150 ml of dimethyl sulfoxide is added 15.0 g of p-tert-butylphenol in 50 ml of dimethyl sulfoxide and 18.9 g of 2-bromopropionic acid in 50 ml of dimethyl sulfoxide. The mixture is stirred at room temperature for 1/2 hr. and heated on a steam bath overnight. The mixture is diluted with 250 ml of water, acidified with 10 ml of conc. hydrochloric acid and extracted with ether. The ether extracts are dried (MgSO4) and the solvent removed under vacuum. Chromatography over silica gel with dichloromethane as eluent gives the product as white crystals, mp 86°-89° C.

Provenance & Evidence