Ethanol → alpha-Naphthaleneacetic acid, ethyl ester

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Reaction Steps

100 g (537 mmol) of naphthalene-1-acetic acid in 200 ml of absolute ethanol are heated to 60° C., while stirring, and 80 ml of thionyl chloride are added slowly in such a way that reflux occurs. Reflux is maintained for 6 h, and the solvent is then evaporated under reduced pressure. The residue is taken up with 200 ml of dichloromethane, the solution is washed with a saturated solution of sodium hydrogen carbonate and then with water, dried over magnesium sulphate and filtered, and the solvent is evaporated under reduced pressure. 104 g (485 mmol) of product are obtained in the form of an oil. n25D =1.5800.

Provenance & Evidence