General procedure for the synthesis of 1-(hydroxymethyl)-5,6,7,8-tetrahydronaphthalene from 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid: 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (2.0 g, 11 mmol) was dissolved in tetrahydrofuran (THF, 30 mL), and the borane-THF solution was slowly added at 0°C (23 mL, 0.98 M THF solution. 23 mmol). The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the reaction was quenched by careful addition of water at 0 °C, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with gradient elution from hexane to hexane/ethyl acetate (3:1, v/v) as eluent to give 1-(hydroxymethyl)-5,6,7,8-tetrahydronaphthalene (1.9 g, colorless oil, quantitative yield).
