Synthesis
Sodium borohydride (0.33 g) was slowly added to a methanolic solution (15 ml) of 2,4-dichloroacetophenone (3.0 g) under cooling conditions in an ice bath. The reaction mixture was stirred at room temperature for 30 min before the reaction was terminated by the addition of water (30 ml) followed by extraction with ethyl acetate (30 ml x 2). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using ethyl acetate-hexane (2:1, v/v) as eluent to afford 1-(2,4-dichlorophenyl)ethanol as a colorless oil (3.00 g, 99% yield).1H-NMR (300 MHz, CDCl3) δ: 1.47 (3H, d, J=6.2 Hz), 1.94 (1H, d, J=3.6 Hz ), 5.25 (1H, qd, J=6.3,3.9Hz), 7.23-7.37 (2H, m), 7.55 (1H, d, J=8.0Hz).
References
[1] Patent: EP1829863, 2007, A1
[2] Patent: WO2006/57448, 2006, A1. Location in patent: Page/Page column 116-117
[3] Zhurnal Obshchei Khimii, 1952, vol. 22, p. 489; engl. Ausg. S. 551
[4] Journal of the Chemical Society, Dalton Transactions, 2001, # 20, p. 2989 - 2995
[5] Advanced Synthesis and Catalysis, 2010, vol. 352, # 10, p. 1779 - 1783
