Hydrochloric Acid → 4-Phenoxybutanohydrazide

Participants

Reaction Steps

A mixture of phenol (100 mg), ethyl 5-bromovalerate (222.2 mg), cesium carbonate (693 mg) and DMF (1.6 ml) was stirred at room temperature for 12 h. Ethyl acetate and water were then added to the reaction solution, and the aqueous phase was adjusted to pH 6 with 2N HCl solution. The aqueous phase extracted twice more with ethyl acetate. The combined organic phases were then washed with water and dried over sodium sulfate, and the solvent was removed in vacuo. The product obtained in this way was taken up in abs. ethanol (0.5 ml), 37.3 μl of hydrazine hydrate were added, and the mixture was heated under reflux for 12 h. Ethyl acetate and water were then added to the reaction solution, and the aqueous phase was neutralized with 2N HCl solution. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were then washed with water and dried over sodium sulfate, and the solvent was removed in vacuo. The residue was purified by preparative HPLC. The product with the molecular weight of 208.11 (C11H16ClN2O2) was obtained in this way; MS (ESI): 209.1 (M+H+).

Provenance & Evidence