p-Toluenesulfonic acid → 5-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

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Reaction Steps

1.0 g of p-toluenesulfonic acid is added to 96.2 g (0.80 mol) of 2-(hydroxymethyl)-2-methyl-1,3propanediol in 600 ml of acetone, and the mixture is heated to reflux. After 5 hours, the solution is neutralized while still hot by adding 3.0 g of potassium carbonate, and the mixture is stirred for a further 30 minutes and subsequently allowed to stand at room temperature overnight. The mixture is filtered through kieselguhr, and the solvent is removed by distillation in vacuo, leaving about 180 ml of a turbid, oily residue, which is purified by distillation in a high vacuum, giving 78 g of the alcohol 31 as a colorless, viscous oil.

Provenance & Evidence