Water → 1-Heptanol, 7-bromo-

Participants

Reaction Steps

To a solution of crude 7-bromoheptanal (Enders and Bartzen (1991) Liebigs Ann. Chem, 569-574) (3.32 g, 17.2 mmol) in acetone (50 mL) was added potassium thioacetate (2.36 g, 21 mmol) under stirring at rt. Then the mixture was refluxed, yielding a precipitate after a few minutes. The reaction was monitored by TLC and cooled to rt when no starting material was detectable (4 h). Water (50 mL) was added, the mixture was extracted with ethyl ether until the organic phase was colorless, and the combined organic phases were dried (Na2SO4) and evaporated. Distillation at 98° C. with a water suction pump afforded 1.66 g (51%, 42% from 7-bromoheptanol) of a yellow oil. IR (neat): {tilde over (v)} 2938, 2857, 2721, 1725, 1694; 1H NMR δ 1.28-1.43 (m, 4H), 1.53-1.69 (m, 4H), 2.33 (s, 3H), 2.43 (dt, 3J=7.3Hz, 3J=1.5Hz, 2H), 2.86 (t, 3J=7.3 Hz, 2H), 9.77 (t, 3J=1.5 Hz, 1H); 13C NMR (APT) δ 21.6 (+), 28.1 (+), 28.3 (+), 28.6 (+), 29.0 (+), 30.3 (−), 43.3 (+), 195.4 (+), 202.0 (−); GC-MS (EI) obsd 188, 187, 145, 128, 112, 94, 43.

Provenance & Evidence