Acetic Acid → 2-[2-(Dimethylamino)phenyl]-1,1-diphenylethanol

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Reaction Steps

In a 30 ml Schlenk flask, 0.514 g (3.80 mmol) of N,N-dimethyl-o-toluidine, 0.898 g (7.60 mmol) of α-methylstyrene, 6.60 g of hexane and 4.43 ml (38.0 mmol) of cyclopentyl methyl ether were placed. Then, 4.78 ml (7.60 mmol) of a 1.59M n-butyllithium hexane solution was dropwise added at 25° C., and the mixture was stirred for 13 hours. To the reaction mixture, a diethyl ether solution containing 1.34 g (7.50 mmol) of benzophenone was dropwise added, and the mixture was stirred for 30 minutes. The resulting reaction mixture was added to a diethyl ether solution containing 0.500 g (8.3 mmol) of acetic acid, and the mixture was stirred for 5 minutes. Thereafter, 5 ml of water was added, and the mixture was further stirred for 5 minutes. After the aqueous phase was separated, the organic phase was extracted with 10% hydrochloric acid, and the resulting aqueous phase was neutralized, whereby 2-(2-(dimethylamino)phenyl)-1,1-diphenylethanol was obtained as a white crystal. The yield was 0.680 g and was 56%. Identification was carried out by a 1H-NMR spectrum. The results of the measurement are given below.

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