p-Toluenesulfonic acid → HCID 20370988, compound

Participants

Reaction Steps

A mixture of 12.1 grams (50 millimoles) of α-methylol benzoin, 6.0 grams (50 millimoles) of acetophenone, 1.0 gram of p-toluenesulfonic acid and 100 ml. of benzene was refluxed under a Dean-Stark trap for 2 hours, the mixture allowed to stand overnight at room temperature, then saturated with ammonia gas and filtered. The resulting oil was distilled at 135°-165° C at 20μ vacuum pressure to yield 10.5 grams of an only partially pure product. 7.2 grams of this product were chromatographed on silica gel with 5% diethyl ether-hexane elution to yield 6.2 grams of a product that was still not entirely pure, which was subjected to NMR and infrared examination as follows:

Provenance & Evidence