Dimethyl Sulfate → Methyl 2-(naphthalen-1-YL)propanoate

Participants

Reaction Steps

Into the cathode chamber of an electrolytic cell divided with an ion-exchange resin diaphragm was placed a solution of 10 mmols of methyl 1-naphthylacetate, 12 mmols of dimethyl sulfate and 1.0 g of tetraethylammonium tosylate in 30 ml of acetonitrile. The anode chamber was supplied with a solution of 2.0 g of tetraethylammonium tosylate in 10 ml of acetonitrile. Constant current electrolysis was conducted at 0.2 A/cm2 with use of platinum for both the cathode and the anode. After passing 1.5 F of electricity per mol of the methyl 1-naphthylacetate 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 distilled off and the residue was purified by silica gel column chromatography using hexane-ethyl acetate (10:1), giving methyl 1-naphthyl(α-methyl)acetate in a yield of 92%. The spectral data of the ester were as follows.

Provenance & Evidence