Ethylene Glycol → 2-(3-Chloropropyl)-2-(4-methoxyphenyl)-1,3-dioxolane

Participants

Reaction Steps

A solution of 20.0 g (94.0 mmol) of 4-chloro-1-(4-methoxyphenyl)-1-butanone (origin: Acros), 19 ml of ethylene glycol and ca. 1 g of p-toluenesulfonic acid in 120 ml of toluene was heated under reflux with azeotropic removal of water for 16 h. After cooling down to room temperature, ether was added and the organic phase extracted with a saturated solution of NaHCO3 (2×), washed with water (2×), dried (Na2SO4) and concentrated in vacuo to give 24.6 g (99%) of the crude compound, which was used for further functionalization. Column chromatography of 2 g (SiO2, heptane/ether 9:1) afforded 1.15 g of a slightly yellow oil.

Provenance & Evidence