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

Participants

Reaction Steps

A mixture of 4-bromobenzaldehyde (1 Scheme 18, 9.5 g, 51.4 mmol) and ethylene glycol (6.4 g, 113 mmol) and p-toluenesulfonic acid (120 mg) in benzene (200 mL) was refluxed in a Dean Stark apparatus for 4 h. The reaction mixture was cooled to room temperature, and the solution was extracted with cold water/ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and concentrated to give a colorless oil (11.4, 95%); 1H NMR (300 MHz, CDCl3) δ 4.01-4.14 (4 H), 5.78 (s, 1 H), 7.37 (d, J=8.34 Hz, 2 H), 7.53 (d, J=8.34 Hz, 2 H); HRMS (EI) calcd for C9H9BrO2 227.9786, 229.9766, found 227.9771, 229.9754.

Provenance & Evidence