Chloromethyl Methyl Ether → HCID 13488867, compound

Participants

Reaction Steps

16.1 g of 6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethanol were dissolved in 70 ml of dry dimethylformamide. 3.0 g of a 50% w/w suspension of sodium hydride in oil (which had been washed with cyclohexane 3 times) were added gradually to the resulting solution at 5°-10° C., with stirring and under a nitrogen stream. The mixture was reacted for 1 hour at room temperature, and then the solution was ice-cooled to 3°-5° C., and 5.5 g of chloromethyl methyl ether dissolved in 40 ml of dry benzene were added dropwise. After the whole of this had been added, the solution was reacted for 1 hour at room temperature. The reaction mixture was then poured into ice-water and extracted with cyclohexane. The extract was washed four times with a 5% w/v aqueous solution of sodium hydroxide, and then with water. It was then dried and the solvent was distilled off under reduced pressure, giving the desired 6-(methoxymethoxy)-2,5,7,8-tetramethylchroman-2-ylmethanol. On thin layer chromatography, the Rf value was 0.45 [silica gel; developing solvent:benzene:ethyl acetate=4:1 by volume].

Provenance & Evidence