N,N,N',N'-Tetramethylethylenediamine → (2-Methoxymethoxyphenyl)(2-hydroxy-3-methoxyphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

A 1.6 M solution of butyl lithium (90.6 ml, 0.145 mol) was placed in a flask and blanketed with nitrogen and to this was added with stirring, while maintaining the temperature at 25°-30° C., 16.85 g, (0.145 mol) of tetramethylethylenediamine. The mixture was then cooled to 0° C. and 20.0 g (0.145 mol) of methoxymethoxybenzene was added with stirring and allowed to react for 2 hours after which 10.0 g (0.066 mol) of 2-hydroxy-3-methoxybenzaldehyde was added under the same conditions. The mixture was allowed to react for a few minutes and was then poured into a mixture of ice and saturated aqueous ammonium chloride. The solid that formed, which was insoluble in ether, was collected by filtration to obtain 15.5 g (81 percent of theory) of the title compound. The proton nmr spectrum was consistent with the assigned structure.

Provenance & Evidence