Ethyl Acetate → HCID 57994322, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-hydroxybenzylamine (1 g, 8.1 mmol) in THF (20 ml) and water (20 ml) was cooled down to 0° C. with sodium hydroxide (357 mg, 8.9 mmol). Benzyl chloroformate (1.27 ml, 8.9 mmol) was added slowly and the reaction mixture was stirred at 0° C. for 1 h and at r.t. for 18 hours. Brine (20 ml) and ethyl acetate (20 mL) were added and the phases were separated. The aqueous phase was extracted with EtOAc (20 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness to yield a light pink solid (2.45 g, 100%). 1H NMR (300 MHz, CDCl3), δ: 4.30 (2 H, d, J=5.8 Hz, CH2NH), 5.15 (2 H, s, OCH2), 6.67 (1 H, br. s, NH), 6.78 (2 H, d, J=8.5 Hz, Ar), 7.12 (2 H, d, J=8.1 Hz, Ar), 7.29-7.44 (5 H, m, Ar)

Provenance & Evidence