To the solution of the Grignard reagent, cooled by an
ice-salt bath, a mixture of
21.3 g. (0.3 mole) of methoxyacetonitrile [Org. Syntheses Coll. Vol. 2, 387 (1943)] and
50 ml. of dry ether is slowly added with stirring. The colorless addition product separates at once. After standing at room temperature for 2 hours, the mixture is again cooled and then decomposed by adding, with stirring, 500 ml. of water and cracked ice, and then
100 ml. of cold dilute sulfuric acid (Note
1). When the decomposition is complete (Note
2), the
ether layer is separated and the aqueous layer is extracted with a little
ether. This
ether extract is combined with the
ether layer, and the whole is washed with
5% aqueous sodium carbonate solution and then with water. The solution is dried with anhydrous
sodium sulfate.
The
ether is removed by distillation from a
steam bath, and the residue is distilled under diminished pressure.
ω-Methoxyacetophenone is a colorless liquid which boils at
118–120° /15 mm. or
228–230° /760 mm. (Note
3). The yield is
32–35 g. (
71–78% based on the
methoxyacetonitrile).