Acetone → 5,5-Bis(bromomethyl)-2,2-dimethyl-1,3-dioxane

Participants

Reaction Steps

A solution of 2,2-bis(bromomethyl)-1,3-propanediol (5.0 g, 19.1 mmol), anhydrous acetone (20 mL) and p-TsOH (100 mg) in benzene (75 mL) was refluxed for 12 h, with azeotropic removal of water. The reaction mixture was concentrated under reduced pressure, EtOAc (100 mL) was added and the organic layer was washed successively with H2O (3×30 mL) and brine (30 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The white solid obtained was triturated with n-pentane (20 mL) to afford 5,5-bis(bromomethyl)-2,2-dimethyl-[1,3]dioxane (521) as colourless crystals.

Provenance & Evidence