4-Nitrophenol → 4-Nitrophenyl Propionyloxymethyl Carbonate

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Reaction Steps

4-Methylmorpholine (0.67 mL, 6.0 mmol) is added to a suspension of 4-nitrophenol (0.83 g, 6.0 mmol) in CH2Cl2 (10 mL) with stirring. A solution of 7c (1.27 g, 95% purity, 7.2 mmol) in CH2Cl2 (3 mL) is added during 20 min followed by stirring at 0° C. (30 min) and overnight at room temperature. After filtration the filtrate is evaporated and the residue partitioned between ice-cold Et2O (25 mL) and H2O (25 mL). The organic phase is extracted with ice-cold 0.5N NaOH (10 mL), H2O (3×15 mL), dried (MgSO4) and evaporated. The residue (1.50 g) is extracted with hexane (2×10 mL) to leave the title compound (0.98 g, 61%), mp 35°-36° C.

Provenance & Evidence