Hydrochloric Acid → HCID 73880358, compound

Participants

Reaction Steps

Potassium tert-butoxide (0.044 mol, 44mL 1M solution in THF) was added to a mixture of terephthalaldehyde mono-(diethyl acetal) (Sigma-Aldrich) (9.98 g, 0.048 mol) and 4-(diphenylamino)benzyltributylphosphonium bromide (21.6 g, 0.040 mol) in anhydrous THF (200 mL) in a 500 mL round bottom flask equipped with a reflux condenser, addition funnel and nitrogen inlet. After the addition was complete, the mixture was refluxed for 2 hours, and then cooled to RT. Aqueous HCl (20 mL, 3M) was then added and the mixture was stirred an additional hour. The product was extracted with methylene chloride (3×100 mL) and the combined organic solution dried with MgSO4. The solvent was removed by rotovaporization and the crude product purified by silica gel column chromatography (1:1 hexane:methylene chloride) yielding the pure product as a bright yellow solid (13 g, 87%). 1H NMR δ: 7.02-7.85 (m, 18 Ar—H, 2 vinyl H), 9.96 (s, 1H, CHO).

Provenance & Evidence