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

Participants

Reaction Conditions

Reaction Steps

A solution of 2,2-dimethyl-[1,3]dioxane-5-carboxylic acid ethyl ester (7.03 g, 37.35 mmol) in tetrahydrofuran (20 ml) was added dropwise to a cooled to 0° C. suspension of lithium aluminum hydride (1.8 g, 48.55 mmol) in tetrahydrofuran (20 ml). The reaction was stirred at 0° C. for 20 min and at 25° C. for 2 h. After such time, ethyl acetate (1 ml) and a few crystals of sodium sulphate decahydrate were added with caution. After stirring at 25° C. for 1 h saturated sodium chloride solution was added and the product extracted with ethyl acetate (3×100 ml). The organics were washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo to afford (2,2-dimethyl-[1,3]dioxan-5-yl)-methanol (4.09 g, 76%) as a clear oil: 1H NMR (300 MHz, CDCl3) δ ppm 1.39 (s, 3H, CH3), 1.44 (s, 3H, CH3), 1.79-1.90 (m, 1H, CH), 2.15-2.26 (brs, 1H, OH), 3.69-3.81 (m, 2H, 2×OCH of 2×OCH2), 3.74 (d, J=6.8 Hz, 2H, OCH2), 3.96-4.05 (m, 2H, 2×OCH of 2×OCH2).

Provenance & Evidence