Benzaldehyde → 4-Hydroxymethyl-2-phenyl-1,3-dioxane

Participants

Reaction Steps

A mixture of 1,2,4-butanetriol (3.0 g, 28.3 mmol) and benzaldehyde (11.48 ml, 113 mmol) in dry toluene (50 mL) with p-toluenesulfonic acid monohydrate (0.269 g, 1.413 mmol) was heated under reflux in a Dean-Stark apparatus. After ˜1 h, the solution was washed with sat. aq NaHCO3, dried and concentrated under high vac to remove most of the benzaldehyde. Chromatography gave syrupy title compound (2.88 g, 14.83 mmol, 52.5% yield). The NMR's were the same as reported (Tetrahedron Asymm. 1996, 7, 3209-3246).

Provenance & Evidence