m-Chloroperbenzoic acid → 1-Hydroxytridecan-2-one

Participants

Reaction Conditions

Reaction Steps

3-Chloroperoxybenzoic acid is added in one portion to a cooled (0° C.) solution of 2-trimethylsilyloxy-1-tridecene in hexane (200 mL). The ice bath is removed and the resulting slurry is stirred (4 hours, 25° C.). Ether (200 mL) and 1.5 N HCl (130 mL) are added and the resulting two-phase mixture is stirred vigorously (4.5 hours, 25° C.). The layers are separated and the organic layer is washed with saturated sodium bicarbonate (2×130 mL), washed with brine (1×130 mL), dried (MgSO4), and concentrated in vacuo. The residue is chromatographed on silica (90:10 hexane:ethyl acetate), and concentrated in vacuo. The resulting solid is washed with cold hexane and collected by filtration to yield 1.5 g (29%) of the title compound as white platelets, m.p. 52°-54° C.

Provenance & Evidence