Hydrochloric Acid → 3-(4-(tert-Butoxy)phenyl)propanoic acid

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Reaction Steps

2.86 g (8 mmol) of 3-(4-tert.butoxyphenyl)-propionic acid 4-nitrobenzyl ester in 500 ml of dioxan are saponified while stirring with 8 ml of 2-N sodium hydroxide for 2 hours at 70° C. and for 12 hours at room temperature. After acidifying the solution with an equivalent amount of 1-N hydrochloric acid, the organic solvent is almost completely removed in vacuo and the residue partitioned between 40 ml of 0.5-N potassium hydrogen carbonate solution and diethyl ether. After cooling, the aqueous phase is cautiously acidified with 1-N hydrochloric acid and extracted several times with ethyl acetate. The combined organic phases are washed neutral with water, dried over sodium sulphate and evaporated in vacuo. A solution of the residue in heptane is filtered and evaporated to dryness in vacuo. There is obtained 3-(4-tert.butoxyphenyl)-propionic acid in the form of a crystalline residue of melting point 29°-31° C. The product is chromatographically pure in cyclohexane/chloroform/acetic acid (45:45:10). The yield amounts to 1.3 g (73% of theory).

Provenance & Evidence