2,2-Dimethoxypropane → (2,2-Dimethyl-1,3-dioxan-5-yl)methanol

Participants

Reaction Steps

2-(Hydroxymethyl)-1,3-propanediol (1.0 g, 9.4 mmol), 2,2-bis(methyloxy)propane (2.3 mL, 18.8 mmol) and p-toluenesulfonic acid monohydrate (0.09 g, 0.5 mmol) were dissolved in THF and stirred for ˜60 h. To the solution was added triethyl amine (1.0 mL) and the solvent was evaporated. Purification was accomplished by column chromatography (CH2Cl2:MeOH) to afford the title compound (0.6 g, 44%) as a oil. 1H NMR (400 MHz, DMSO-d6): δ ppm 4.52 (t, 1H), 3.80 (dd, 2H), 3.59 (dd, 2H), 3.36 (dd, 2H), 1.63-1.72 (m, 1H), 1.28 (d, 6H).

Provenance & Evidence