Phenol → HCID 12196105, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-chloro-4-nitrobenzoic acid (3 g, 14.9 mmole) and phenol (3 g, 31.9 mmole) in MeOH (20 mL) was added a solution of NaOMe in MeOH (25 wt %, 9 mL, 39.4 mmole). After 15 minutes the solution was concentrated to dryness and the residue was taken up in dimethylacetamide (50 mL). Copper powder (100 mg) was added and the mixture was heated at reflux with stirring (180° C. oil bath). After 1 hr the reaction was cooled to RT, acidified with 1.0 N HCl (40 mL), and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), and concentrated under vacuum. The remaining residue was triturated with 1:1 Et2O/petroleum ether and dried under vacuum to afford the title compound (4.65 g). This was used without further purification.

Provenance & Evidence