Potassium Carbonate → HCID 11565461, compound

Participants

Reaction Steps

To a 250 mL flask, equipped with a reflux condenser, magnetic stirrer, and under inert atmosphere, was added 2-benzyloxy-phenol (8.0 g, 40 mmol), 4-bromobutanoic acid ethyl ester (5.7 mL, 40 mmol), potassium carbonate (7.2 g, 52 mmol), and ethanol (100 mL). The reaction mixture was heated to reflux with stirring for 8 hours. The reaction was cooled to room temperature and the insoluble byproduct was removed by suction filtration. 2N aqueous sodium hydroxide (30 mL) was added to the filtrate. This solution was heated to 50° C. for 2 hours. The solution was cooled to room temperature, the ethanol removed under reduced pressure, and the resulting solution was adjusted to pH 9. The aqueous solution was washed with ethyl acetate (2×30 mL) and residual ethyl acetate was removed under reduced pressure. The solution was cooled to 0° C. with an external ice bath and then acidified to pH 2 with 6N aqueous hydrochloric acid. The precipitated product was collected by suction filtration and dried under vacuum. The product (7.2 g, 63%) was isolated as a white powder. 1H-NMR (400 MHz, DMSO-d6): δ 12.0, s, 1H(COOH); δ 7.4, multiplet, 5H (Benzylic aryl H's); δ 7.0, multiplet, 2H (Aryl H's); δ 6.9, multiplet, 2H (Aryl H's); δ 5.0, s, 2H (Benzylic CH2); δ 4.0, t, 2H (CH2 α to phenoxy); δ 2.4, t, 2H(CH2 α to COOH); δ 1.9, multiplet, 2H (remaining CH2 group).

Provenance & Evidence