1-Naphthaleneacetic Acid → N-(2-hydroxy-1,1-dimethyl-2-phenylethyl)-2-(1-naphthyl)acetamide

Participants

Reaction Conditions

Reaction Steps

A solution of 74.5 g. (0.4 mole) of 1-naphthyl acetic acid, 111.0 g. (0.45 mole) of EEDQ and 66.0 g. (0.4 mole) of α-(1-amino-1-methylethyl)benzenemethanol in 1 l. tetrahydrofuran is stirred and heated for 2 hours at 65° C. and then allowed to stand for 20 hours at room temperature. THF is evaporated in vacuo, and the residue is taken up with ice and 10% aqueous H2SO4 solution to pH 2. The resulting amide is extracted twice with 750 ml. ethyl acetate. The combined organic extracts are washed with 500 ml. dilute NaHCO3, dried (Na2SO4) and evaporated to dryness in vacuo. The oil is dissolved in 1 l. hot isopropyl ether and on standing at 25° C. gives 101.0 g. (77% yield) of N-(2-hydroxy-1,1-dimethyl-2-phenylethyl)-1-naphthaleneacetamide as an off-white crystalline solid of analytical purity, m.p. 106°-107° C.

Provenance & Evidence