Trifluoroacetic acid → 4-Chloro-2-ethylphenol

Participants

Reaction Steps

To a stirred solution of 1.7 g (9.96 mmol) of 1-(5-chloro-2-hydroxyphenyl)ethanone in 20 mL of CH2Cl2 and 11.34 g (99.47 mmol) of trifluoroacetic acid, slowly add 3.46 g of (29.82 mmol) of triethylsilane. Stir resulting solution at room temperature for 18 hours, and remove volatiles and excess reagents under reduced pressure to give 1.52 g (97.4%) of 4-chloro-2-ethylphenol as an oil. 1H NMR (500 MHz, CDCl3) δ 7.09 (d, J=2.6 Hz, 1H), 7.03-7.01 (m, 1H), 6.65 (d, J=8.5 Hz, 1H), 4.82 (s, 1H), 2.58 (q, J=7.6 Hz, 2H) and 1.21 (t, J=7.6 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 151.85, 131.82, 129.62, 126.62, 125.60, 116.28, 22.81 and 13.60. MS m/e 157. The 4-chloro-2-ethylphenol can be used in Preparation 13b.

Provenance & Evidence