Nitrogen → HCID 86666550, compound

Participants

Reaction Conditions

Reaction Steps

To a single necked round bottomed flask (500 mL) fitted with N2(g) balloon, Methyl 3-benzyloxy-5-hydroxybenzoate (Intermediate 5) (24 g, 93 mmol, 1 equiv.) followed by DMF (130 mL, 5 v/w) were added. To this stirring solution, potassium carbonate (38 g, 279 mmol, 3 equiv.) was added at room temperature. The mixture was stirred at the same temperature for 10 minutes. 4-Fluorobenzaldehyde (13.84 g, 111.62 mmol, 1.2 equiv.) was added. The reaction mixture was heated at 90° C. for 16 h. The progress of the reaction was monitored by TLC. After completion, the reaction was diluted with water and extracted with ethyl acetate. Combined organic layers were washed with brine and dried over anhydrous sodium sulphate to furnish title compound as thick yellow liquid (32.5 g). The product can be purified by column chromatography by eluting with 10% ethyl acetate:pet ether as mobile phase.

Provenance & Evidence