Hydrochloric Acid → HCID 15491199, compound

Participants

Reaction Steps

A solution of 4,4-bis-(4-hydroxyphenyl)pentanoic acid (2.00 g, 6.99 mmol) in 40 mL anhydrous tetrahydrofuran was treated with carbonyl diimidazole (3.76 g, 23.2 mmol) and the resulting solution heated at reflux under a N2 atmosphere for 24 hours. Dibenzylamine (5.38 mL, 28 mmol) was then added, and the reaction refluxed again for 48 hours. The reaction mixture was cooled and treated with 10% aqueous HCl solution (50 mL), followed by water (100 mL) and ethyl acetate (200 mL). The organic phase was collected and washed sequentially with water (100 mL) and brine (100 mL). The organic phase was dried (MgSO4), filtered and concentrate. The residue was purified by chromatography (silica gel, 50% ethyl acetate/hexane) to give the title compound (1.30 g, 40%) as a solid, mp=203-207° C.

Provenance & Evidence