Phenol → 29488-54-8

Participants

Reaction Steps

N-(2-Phenoxyethyl) morpholine was prepared by a modified method of Grail. et al (Journal of American Chemical Society, 1952, 74, 1313-1315). For example, 9.2 g of phenol and 18.6 g of N-(2-chloroethyl)morpholine HCl salt were dissolved in 120 ml of isopropanol and 12 g of potassium hydroxide was added with cooling. The reaction mixture was refluxed for 12 hours. Solid (KCl) was filtered off. The filtrate was distilled off. The residual material was treated with 150 ml of 1N NaOH, then, extracted with dichloromethane (200 ml). Dichloromethane layer was again washed with a solution of 0.1N sodium carbonate in 10% NaCl solution. Dichloromethane layer was dried over anhydrous magnesium chloride, and evaporated under reduced pressure. Residual syrup was dissolved in 100 ml of 1.5N HCl solution, and washed with 100 ml of chloroform. Aqueous layer was treated with 100 ml of toluene and water was removed by Dean-Stark apparatus by distillation. Residual toluene layer was cooled to give crystalline solid, which was collected by filtration. 12 g of N-[(2-phenoxy)ethyl]morpholine HCl salt (50% yield )was obtained.

Provenance & Evidence