Synthesis
General procedure for the synthesis of 2-(3,4-dichlorophenyl)ethanol from 3,4-dichlorophenylacetic acid: 97% lithium aluminum hydride (LiAlH4, 5.54 g, 141.63 mmol) was added batchwise to an ice-bath-cooled solution of 2-(3,4-dichlorophenyl)acetic acid (19.36 g, 94.42 mmol) in tetrahydrofuran (THF, 200 mL). After the addition was completed, the reaction mixture was stirred at room temperature for 5 hours. Upon completion of the reaction, the mixture was slowly poured into ice water (150 mL) and stirring was continued for 0.5 hours. Subsequently, THF was evaporated under reduced pressure and extracted by adding dichloromethane (DCM, 200 mL). The organic layer was separated, washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/5, v/v) to afford the target compound 2-(3,4-dichlorophenyl)ethanol (17.14 g, 95% yield) as a colorless oil.
References
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[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 3, p. 756 - 760
[5] Journal of the American Chemical Society, 1956, vol. 78, p. 5612
