Ethylene Glycol → HCID 19434044, compound

Reaction equation

[Br:1][C:2]1[CH:6]=[C:5]([Br:7])[S:4][C:3]=1[CH:8]=[O:9].[CH2:10](O)[CH2:11][OH:12]>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:6]=[C:5]([Br:7])[S:4][C:3]=1[CH:8]1[O:12][CH2:11][CH2:10][O:9]1

Participants

Procedure

A mixture consisting of the product from Step A (11.0 g, 40.7 mmol), TsOH (0.25 g) and ethylene glycol (5.06 g, 81.5 mmol) in toluene (150 mL) was heated at reflux temperature for 1.5 h, water was removed by a Dean-Stark trap. The reaction mixture was cooled and poured into a saturared aqueous solution of sodium bicarbonate (100 mL). The organic layer was separated, dried (MgSO4), and evaporated to dryness. Purification of this crude material by column chromatography (silica, 6% ethyl acetate/hexane) gave 10.33 g of an oil (81%).