A 70% solution of sodium bis (2-methoxyethoxy)-aluminum hydride in benzene (35 ml.) was stirred with ice bath cooling while a solution of 20.55 g. (0.0558 mole) of (S)-(-)-methyl-6-benzyloxy-2,5,7,8-tetramethyl- chroman-2-acetate in 50 ml. of benzene was added dropwise over 80 minutes keeping the temperature below 20° C. The resulting solution was stirred at room temperature for 2 hours then cautiously poured onto a mixture of ice and 1 N aqueous NaOH. Work-up by means of ether extraction in the manner of Example 1 afforded 19.8 g. of viscous colorless oil. This material was triturated with petroleum ether (30°-60° C.) and the resulting solid was filtered, washed with petroleum ether and dried under high vacuum giving 14.95 g. (78.7%) of (S)-(-)-6-benzylosy-2,5,7,8-tetramethyl-chroman-2-ethanol as a colorless solid, m.p. 55°-56° C.; [α]25D - 16.21° (c 2.03, CHCl3).
