2-Naphthol → Binol

Participants

Reaction Steps

A two-neck round bottom flask (5 mL) was charged with a solution of catalyst 1c (12.2 mg, 0.02 mmol) in anhydrous CCl4 (1 mL). The solution was stirred for 10 min under an oxygen atmosphere and then treated with a solution of 2-naphthol (29 mg, 0.2 mmol) in anhydrous CCl4 (1 mL). The reaction mixture was stirred at 0° C. until the reaction was complete (monitored by TLC). The crude mixture was concentrated under reduced pressure, and purified by column chromatography (Ethyl acetate/Petroleum ether=⅓) to give (R)-BINOL 3a, Yield 84%. 1HNMR (300 MHz, CDCl3) δ (ppm) 7.98 (d, J=9.0 Hz, 2H, 2×HC (4)), 7.90 (d, J=7.8 Hz, 2H, 2×HC (5)), 7.38 (d, J=9.0 Hz, 2H, 2×HC (8)), 7.41–7.27 (m, 4H, 2×HC (6), 2×HC (7)), 7.16 (d, J=8.4 Hz, 2 H, 2×HC (3)), 5.09 (s, 2H, 2×OH). e.e. 90% and the configuration was R (Kromasil CHI-TBB column, Hexane/propan-2-ol=90: 10; flow rate 1 mL/min; S-isomer, tR 7.78 min and R-isomer, tR 8.79 min).

Provenance & Evidence