Dimethyl Sulfoxide → Diphenoxymethane

Participants

Reaction Steps

To m-methoxyanisole (100 g) in DMSO (350 ml) was added 39 g sodium hydride (50%) in portions. The solution was stirred at room temperature under nitrogen overnight. 4-Trifluoromethyl-1,2-dichlorobenzene (173.2 g) was added to the solution in one portion, followed by copper powder (2 spatulas) and 18-crown ether (i,4,7,10,13,16-hexaoxacyclooctadecane, 2 g). The slurry was kept 152°-170° under nitrogen for 24 hours, then added to ice (1.5 l). The mixture was allowed to stand until the ice melted, then filtered. The solid which was collected was dissolved in methylene chloride (1.5 l) and filtered. The aqueous filtrate was extracted with methylene chloride (500 ml) and the methylene chloride phase was washed with water, dried (MgSO4), filtered and stripped to yield a dark oil. The other methylene chloride solution (1.5 l) was washed with water, dried (MgSO4), filtered and stripped to yield an oil. Both oil fractions were treated with petroleum ether and filtered. The filtrates were combined and stripped to yield the phenoxy methoxybenzene product, 244 g.

Provenance & Evidence