2-naphthalen-1-ylpropan-2-ol

90-11-9

67-64-1

6301-54-8

To a stirred solution of dry THF (400 mL) of 1-bromonaphthalene (12, 41.41 g, 0.2 mol) held at -78 °C under N2 atmosphere, a hexane solution (125 mL, 0.2 mol) of 1.6 M n-BuLi was slowly added dropwise via syringe. After the dropwise addition, the resulting solution was continued to be stirred at -78 °C for 1 hour. Subsequently, dry acetone (17.42 g, 0.3 mol) was added dropwise via syringe to the reaction system. The reaction mixture was stirred at -78 °C for 0.5 h. After that, it was brought to room temperature and stirring was continued for 1 h. The reaction mixture was then stirred at -78 °C for 0.5 h. The reaction mixture was slowly poured into ice water (2 L), stirred and extracted with CH2Cl2 (500 mL × 3). The organic phases were combined, washed with 5% brine (500 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography and then milled with n-hexane/EtOAc (1:100, v/v) to obtain the pure 2-(naphthalen-1-yl)-2-propanol (13) as colorless needle-like crystals (33.90 g, 91%). Melting point: 88.5-90°C (literature value: 83-85°C [18]).1H NMR (DMSO-d6, 400 MHz) δ: 8.84-8.87 (m, 1H), 7.87-7.90 (m, 1H), 7.78 (d, 1H, J = 8.0 Hz), 7.56 (dd, 1H, J = 0.8, 7.6 Hz), 7.43-7.49 (m, 2H), 7.40 (t, 1H, J = 7.8 Hz), 5.24 (s, 1H), 1.70 (s, 6H).