2-Trifluoromethylphenol → 1-[(1R)-3-Chloro-1-phenylpropoxy]-4-(trifluoromethyl)benzene

Participants

Reaction Steps

The title compound was prepared by the method of example 55 using [S]-3-chloro-1-phenylpropanol (2.57 g, 15 mmol), α,α,α-trifluoro-cresol (2.4 g, 15 mmol) in THF (40 ml) at room temperature. Workup provided the optically pure title compound as a thick liquid, bp 180°-200° C./0/5 mm. [α]D +2.3° (c 10, CHCl3 ; 13C NMR (CDCl3): 140.50, 129.39, 128 66, 127,56, 127.38, 127.19, 127.01, 126.34, 116.45, 77.82, 41.69, 41.38. Mass spectrum (El): 153/155 (45), 91 (100). (Cl): 314/316, (1, M+), 153/155 (100). Anal. Calcd. for C16H14ClNO: C, 61.05; H, 4.45; Cl, 11.29; F, 18.12. Found: C, 61.06; H, 4.51; Cl, 11.16; F, 8.22.

Provenance & Evidence