Triethylamine → (2,2,5,5-Tetramethyl-1,3-dioxolan-4-yl)methanol

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Reaction Steps

A solution of 1.2 g of (RS)-3-methyl-1,2,3-butanetriol in 20 ml of acetone is treated with 0.010 g of anhydrous p-toluenesulphonic acid and left at room temperature for 5 days. After the addition of 0.3 ml of triethylamine, the mixture is evaporated at 30°/11 Torr and the residue is distilled at 130°/11 Torr. The distillate (1.55 g) gives, after chromatography on 90 g of neutral aluminium oxide (activity III) with methylene chloride, as the non-polar fraction 0.81 g of (RS)-α,α,2,2-tetramethyl-1,3-dioxolane-4-methanol and as the polar fraction 0.52 g of the desired product.

Provenance & Evidence