3-Chlorophenethylalcohol

1878-65-5

5182-44-5

Example 86A Synthesis of 2-(3-chlorophenyl)ethanol: To a solution of 2-(3-chlorophenyl)acetic acid (11.4 g, 66.7 mmol) dissolved in 150 mL of THF was added LiAlH4 (3.04 g, 80.0 mmol) in batches at 0 °C. The reaction mixture was gradually warmed up to room temperature and stirred continuously under nitrogen protection for 2 hours. Upon completion of the reaction, the reaction was quenched by slow dropwise addition of 2N NaOH solution (30 mL), followed by extraction with ethyl acetate (2 x 150 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography (silica gel as stationary phase, petroleum ether/ethyl acetate = 50:1 to 10:1 gradient elution) to give 4.96 g of the target product, 3-chlorophenethyl alcohol, as a colorless oil. The yield was 55%.