Methyl Methanesulfonate → 2-Phenylpropionic acid

Beteiligte Stoffe

Reaktionsschritte

Into the cathode chamber of an electrolytic cell divided with an ion-exchange resin diaphragm was placed a solution of 10 mmols of methyl phenylacetate, 12 mmols of methyl methanesulfonate and 1.0 g of tetraethylammonium tosylate in 30 ml of anhydrous dimethylformamide. And the anode chamber of the electrolytic cell was supplied with a solution of 3.0 g of tetraethylammonium tosylate in 10 ml of anhydrous dimethylformamide. Constant current electrolysis was conducted at 0.2 A/cm2 with use of platinum for both the anode and cathode. After passing 1.5 F of electricity per mol of the methyl phenylacetate through the solution at room temperature, the cathode solution was added to a saturated aqueous solution of ammonium chloride and the mixture was extracted twice with ether. The ether was removed by distillation and the residue was purified by silica gel column chromatography using hexane-ethyl acetate (10:1), giving methyl α-methylphenylacetate in a yield of 78% and α-methylphenylacetic acid in a yield of 15%. The spectral data of the ester were as follows.

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