2-Methyl-2-butanol → Acetoacetic Acid

Participants

Reaction Steps

Potassium (1 g) was added to 2-methyl-2-butanol (16 ml) under a nitrogen atmosphere. The mixture was warmed, at 80°, until all the metal had reacted. The excess alcohol was removed by vacuum distillation and the dry residue was dissolved in dry benzene (45-ml). Two ml of this solution were added to HU-211- (30 mg, 0.78 mmoles) dissolved in dry benzene (30 ml). The solution was stirred, under a nitrogen atmosphere, for 2 hrs., then it was washed with a dilute HCl solution (1N), followed by a sodium bicarbonate solution (1N) and then with water. The organic layer was dried over MgSO4, and evaporated. The oil obtained was chromatographed on silica gel (15 gr.) Elution with ether:petroleum ether (1:10) gave the diacetate of HU-211 (99 mg) followed by traces of the monoacetate (on the allylic alcohol moiety), eluted with ether:petroleum ether (2:10), followed by the monoacetate (4c), 150 mg, identified by the I.R. peak at 1760 cm-1 ; 1H NMR δ 2.28 (3H, s, OCOCH3), 2.98 (1H, dd, C-2 equat. H), 4.02 (2H, q, C-7H), 5.72 (1H, d, C-6H), 6.52, 6.66 (atom. H).

Provenance & Evidence