Water → HCID 20326573, compound

Participants

Reaction Steps

Jones' reagent was prepared by dissolving chromium trioxide (26.7 g.) in concentrated sulphuric acid (23 ml.) and making the solution up to 100 ml. total volume with water. This solution was added with stirring to a solution of 1-bromo-3-(3-chlorophenoxy)propan-2-ol (53.0 g.) in toluene (75 ml.) and acetone (50ml.) under an atmosphere of nitrogen, at such a rate as to keep the temperature between 0 and 5° C. When the addition was complete, the reaction mixture was allowed to warm to room temperature and was stirred at that temperature for 16 hours. Toluene (50 ml.) and water (50 ml.) were added to the mixture and the organic layer was separated and shaken with saturated sodium bicarbonate solution (50 ml.). The whole mixture was filtered through "Hyflo" (trade mark) kieselguhr, and the aqueous layer was separated and discarded. The organic layer was washed with water (50 ml.) and dried over magnesium sulphate, and the solvent was removed under reduced pressure at a temperature below 60° C., to give a residue of 1-bromo-3-(3-chlorophenoxy)propan-2-one; the n.m.r. spectrum in deuteriochloroform showed characteristic peaks at:

Provenance & Evidence