Acetone → 3-(4-[1,3]Dioxan-2-yl-2,6-dimethyl-phenyl)-propane-1,2-diol

Participants

Reaction Steps

A solution of 2-(4-allyl-3,5-dimethyl-phenyl)-[1,3]dioxane (790 mg, 3.4 mmol) in acetone (10 mL) is treated with OsO4 (1 mL of a 2.5% solution in tert.butanol), NMO hydrate (551 mg, 4.08 mmol) and water (0.5 mL). The mixture is stirred at rt for 2.5 h before it is diluted with DCM, washed with 10% aq. citric acid solution (2×50 mL), dried over MgSO4, filtered and evaporated. The product is crystallized from DCM/heptane to give 3-(4-[1,3]dioxan-2-yl-2,6-dimethyl-phenyl)-propane-1,2-diol (335 mg) as a grey powder; 1H NMR (CDCl3): δ 7.15 (s, 2H), 5.42 8 s, 1H), 4.26 (dd, J=4.6, 10.6 Hz, 2H), 3.98 (dt, Jd=1.8 Hz, Jt=12.3 Hz, 2H), 3.92-3.81 (m, 2H), 3.66 (dd, J=2.9, 11.1 Hz, 1H), 3.55 (dd, J=7.0 11.1 Hz, 1H), 2.88 (dd, J=8.8, 14.1 Hz, 1H), 2.74 (dd, J=5.3, 13.5 Hz, 1H), 2.34 (s, 6H), 2.30-2.14 (m, 2H), 1.90 (s br, 2H).

Provenance & Evidence