p-Toluenesulfonic acid monohydrate → HCID 86751242, compound

Participants

Reaction Steps

A solution of 1.72 g of (E)-2-[4-(5-but-1-enyl-1,3-dioxan-2-yl)butyl]-1,3-propanediol and 1.0 g of 3,4-difluorobenzaldehyde in 30 ml of benzene is heated to slight boiling with 35 mg of p-toluenesulfonic acid monohydrate for 1 hour. After neutralization of the solution with a few drops of triethylamine the mixture is washed with water, dried over sodium sulfate, filtered and the filtrate is evaporated. The crude product is chromatographed on 40 g of silica gel with hexane/ethyl acetate 5% (v/v). Two-fold crystallization of the resulting isomer mixture from hexane yields pure (E)-trans-2-(3,4-difluorophenyl)-5-[4-(trans-5-but-1-enyl-1,3-dioxane.

Provenance & Evidence