Diacetamate → 4-(Ethylamino)phenol

Participants

Reaction Steps

Five g of this 4-acetoxyacetanilide (0.0259 moles) was dissolved in 200 ml of dry tetrahydrofuran (THF). To this mixture was added slowly, over one-half hour, 1.97 g (0.0518 moles) of lithium aluminum hydride. After the addition of this reagent, the reaction was refluxed for three hours, cooled, and saturated ammonium chloride solution was slowly added. The resultant mixture was filtered, evaporated to dryness and the remaining oil was dissolved in dilute HCl. This solution was extracted with chloroform several times. The remaining aqueous phase was made basic with sodium carbonate to achieve approximately pH 10 and extracted once again with chloroform. The chloroform solution was dried over anhydrus magnesium sulfate and evaporated to dryness. This acid/base extraction procedure was repeated several time to yield 2.2 g of p-ethylaminophenol, as an oil which solidified upon standing.

Provenance & Evidence