Ethylene Glycol → 2-[(4-bromophenyl)methyl]-1,3-dioxolane

Participants

Reaction Steps

A solution of 4-bromophenylacetaldehyde from Step 1 (44.5 g, 224 mmol), ethylene glycol (13.7 mL, 246 mmol) and p-toluenesulfonic acid monohydrate (85 mg, 0.45 mmol) in toluene (300 mL) was refluxed for 3 h with concomitant Dean-Stark water trapping. The reaction mixture was then washed successively with 5% aqueous NaHCO3 (2×), water and brine, dried (MgSO4) and concentrated. The residue was distilled under reduced pressure (bp 110°-115° C./0.5 mmHg) to afford the title compound as a colorless liquid (30.0 g, 55%).

Provenance & Evidence