Ammonia → 1-(4-Bromo-2,6-dimethylphenoxy)-2-methoxyethane

Beteiligte Stoffe

Reaktionsschritte

A solution of 2-(4-bromo-2,6-dimethylphenoxy)ethanol (15 g) in methylene chloride (100 ml) was added to a stirred solution of sodium hydroxide (50 g) in water (50 ml) at 5° C. Dimethyl sulphate (8.6 ml) was added dropwise to the stirred solution at 5° C. over 30 minutes. The mixture was stirred at ambient temperature for 12 hours. Dimethylsulphate (5 ml) was added at ambient temperature and the mixture stirred for a further 2 hours. The mixture was cooled to 0° C. and a solution of ammonia (10 ml, density=0.88 g/cm3) was added. The mixture was stirred for 20 minutes, diluted with iced water (500 ml). The methylene chloride phase was removed and the aqueous phase extracted with methylene chloride (2×150 ml). The organic extracts were combined, washed with water (2×100 ml), saturated brine (100 ml) and evaporated. The residue was distilled using a short path distillation apparatus (furnace temperature 120° C./0.08 bar) to give 1-(4-bromo-2,6-dimethylphenoxy)-2-methoxyethane (11.6 g); NMR(CDCl3): 2.34(6H,s), 3.52(3H,s), 3.78(2H,m), 3.96(2H,m) and 7.2(2H,s).

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