Ethanol → 2-(Phenylmethoxy)-1,3-propanediol

Participants

Reaction Steps

A mixture of about 338 g of 5-(benzyloxy)-2-phenyl-m-dioxane, about 1500 ml of ethanol, about 500 ml of water and about 20 ml of sulfuric acid was refluxed for about 2 hours. The ethanol was removed, the acid neutralized with solid sodium bicarbonate, the mixture steam distilled to remove benzaldehyde and then saturated with potassium carbonate. This mixture was extracted three times with ether. The ether extracts were combined, dried and evaporated. Toluene was added and evaporated. The residue was distilled via a Kugelrohr (about 0.1 mm, 170° C.) giving an oil. This oil was dissolved in about 300 ml of toluene, cooled and diluted with two volumes of petroleum ether. Refrigeration produced about 184.69 g of the desired title compound as a solid.

Provenance & Evidence