Acetone → 5-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

Participants

Reaction Steps

A mixture of 30 g of 1,1,1-tris(hydroxymethyl)ethane (Aldrich Chemical Co., Milwaukee, WI), 85 ml of acetone and 80 ml of petroleum ether (b.p. 30°-75° C.) was acidified with 1.0 g of p-toluenesulfonic acid monohydrate and this mixture was refluxed for 24 hours with removal of water by azeotropic distillation. This was followed by neutralization with 1 g of sodium acetate and complete drying with anhydrous sodium sulfate. The liquid was filtered and the solvents removed under reduced pressure. The residue was distilled under vacuum to give 5-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane in 90% yield.

Provenance & Evidence