Ozone → 1-Heptanol, 7-bromo-

Participants

Reaction Conditions

Reaction Steps

A solution of 8-bromo-1-octene (5.0 g, 26 mmol) in a mixture of 25 mL of MeOH and 5 mL of CH2Cl2 was cooled to -50° C. and treated with O3 until a blue color persisted (45 min) and then for an additional 10 min. The mixture, at -40° C., was purged with N2 for 10 min, allowed to warm to -20° C., under N2, and kept at -20° C. while 1.3 g (34 mmol) of sodium borohydride was added in portions over 30 min (evolution of H2 was evident at each addition). The mixture was stirred 30 min more at -20° C. and quenched with the dropwise addition of 20 mL of H2O. This mixture was stirred for 10 min, and extracted with hexane; the organic extracts were washed with water, then brine, dried (Na2SO4) and concentrated to give 3.65 g (72%) of 7-bromo-1-heptanol: NMR (CDCl3) δ1.44 (m, 9H), 1.85 (m, 2H), 3.41 (t, 2H), 3.65 (t, 2H).

Provenance & Evidence