1-Methoxy-2-phenylethaniMiniuM chloride

Preparation

To a 50-ml pear-shaped flask equipped with a water-reflux condenser, a gas inlet tube reaching the bottom of the flask, and a gas outlet tube fitted with a drying tube is added 2.85 ml (2.90 g, 24.7 mmol) of phenylacetonit-rile, 1.00 ml of dry methanol (0.80 g, 24.7 mmol) and 7 ml of anhydrous ether. The flask is cooled in an ice bath while dry hydrogen chloride gas (first passed through sulfuric acid) is passed into the solution until no more was absorbed.The flask is then disconnected, stoppered tightly, and stored at -10°C overnight. A solid forms, which is isolated by filtration under a stream of argon gas and then dried under reduced pressure for 4 hrs, to yield 4.30 g (23.2 mmol or 94% yield) of a white free-flowing powder. The NMR (CDCI3, 90MHz) indicated 7.32 (m, 5H), 4.23 (s, 3H), 4.05 (s, 2H).