Sodium Hydroxide → 215316-49-7

Participants

Reaction Steps

Ethyl-3-hydroxy-3-(2-phenylethyl)hexanoate (II, EXAMPLE 1,200 mmol) is dissolved in methanol (423 ml) and 2M sodium hydroxide (150 ml, 300 mmol) is added. The reaction mixture is stirred at 20-25° overnight. Methanol is removed and the remaining aqueous mixture is acidified with hydrochloric acid (4 M). The desired product is extracted into methyl t-butyl ether and dried over magnesium sulfate. The product is concentrated to give the title compound, TLC Rf =0.10 (ethyl acetate/hexane, 30/70); NMR (CDCl3) 7.43-7.13, 2.77-2.62, 2.06, 1.87-1.76, 1.63-1.57, 1.45-1.31 and 0.93 δ; CMR (CDCl3) 176.9, 141.9, 128.4, 128.3, 125.9, 73.4, 42.7, 41.4, 40.9, 31.9, 17.0 and 14.5 δ; MS (CI, ammonia) m/z (relative intensity) 254 (100), 236 (28), 218 (3), 194 (3), 159 (5).

Provenance & Evidence