Hydrochloric Acid → HCID 19744756, compound

Participants

Reaction Steps

A mixture of propen-2-yl 3-benzyloxy-4-(propen-2-yloxy)benzoate (1.0356 g, 3.19 mmol), tris(triphenyl-phosphine)rhodium chloride1 (204 mg, 0.22 mmol) and 1,4-diazabicyclo[2.2.2]octane (74 mg, 0.66 mmol) in ethanol (18 cm3) and water (2 cm3) was heated under reflux under an atmosphere of nitrogen for 16 h. The cooled mixture was poured into 1 M hydrochloric acid (100 cm3), stirred for 60 min, then extracted with dichloromethane (3×100 cm3). The combined extracts were dried over MgSO4 and evaporated to an orange solid which was purified by flash column chromatography (eluent: 1:1 EtOAc:light petroleum) to give 3-benzyloxy-4-hydroxybenzoic acid as an orange solid (650 mg, 83%), m.p. 167.2-171.3° C.

Provenance & Evidence