2-Bromopropane → 3-Methyl-2-phenylbutanoic acid

Participants

Reaction Steps

Into the cathode chamber of an electrolytic cell divided with a diaphragm (asbestos) was placed a solution of 10 mmols of methyl phenylacetate, 12 mmols of isopropyl bromide and 1.0 g of tetramethylammonium tosylate in 30 ml of anhydrous dimethylformamide. Constant current electrolysis was conducted at 0.2 A/cm2 with use of lead for the anode and carbon for the cathode. After passing 1.5 F of electricity per mol of the methyl phenylacetate at 20° to 25° C., the cathode solution was added to a saturated aqueous solution of ammonium chloride and the mixture was extracted twice with ether. The ether was distilled off and the residue was purified by silica gel column chromatography using hexane-ethyl acetate (10:1), giving methyl α-isopropylphenylacetate in a yield of 80% and α-isopropylphenylacetic acid in a yield of 9%. The spectral data of the ester were as follows.

Provenance & Evidence