2,5-Dihydroxybenzoic acid → HCID 23448409, compound

Participants

Reaction Steps

A mixture of 2,5-dihydroxybenzoic acid (4.2 g; 27.5 mmol), 1.8-diazabicyclo[5.4.0]undec-7-ene (4.2 g; 27.5 mmol), potassium iodide (41.0 g; 247 mmol), p-[(8-chlorooctyl)oxy]benzonitrile (6.6 g; 25 mmol) and acetonitrile (100 ml) was heated under reflux for 72 h. The reaction mixture was cooled, poured into water (500 ml) and extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×150 ml), dried over magnesium sulphate and filtered. The solvent was removed in vacuo. The residue was purified by column flash chromatography on silica gel using a toluene/ethyl acetate 80:20 as eluent to give 8.0 g (84%) of 8-(p-cyanophenoxy)octyl 2,5-dihydroxybenzoate.

Provenance & Evidence