n-butyllithium in tetrahydrofuran; diethyl ether; hexane T=-115°C; 1.5 h;

1: 85 percent / n-C4H9Li / diethyl ether; tetrahydrofuran; hexane / 1 h / -115 °C 2: 92 percent / H2O / 168 h / Heating View Scheme

in benzene

sodium hydroxide; dihydrogen peroxide in tetrahydrofuran -100°C, after 15 min warming to room temp. with stirring, keeping overnight, treating with H2O2-NaOH at 0°C, stirring for 1 h at room temp. and for 15 min at 50°C; Aq. phase is satd. with K2CO3, extd. with diethyl ether, combined phases are dried (K2CO3), concd., chromd. (silicagel, ethyl acetate-petroleum ether);