反应详情

A mixture of 10 grams (g) [60 millimoles (mMol)] of 3-hydroxymethyl-2-nitrotoluene (1) (Aldrich Chemical Co., Milwaukee, WI) and 7.9 milliliters (ml) of acrylonitrile was stirred under argon at room temperature. Potassium tert-butoxide [10 milligrams (mg)] was added, followed 90 minutes later by an additional 10 mg portion. After a total of 3 hours, the reaction was quenched by the addition of 0.2 ml of acetic acid. Volatile material was removed under reduced pressure, and the residue chromatographed on 300 g of silica gel eluting with methylene chloride (CH2Cl2). Fractions of approximately 17 ml were collected. Fractions 155-200 were combined and the solvent evaporated to give 12.5 grams (g) (90% yield) of 3-(2-cyanoethoxymethyl)-2-nitrotoluene (2) as a clear oil.

1. customAfter a total of 3 hours, the reaction was quenched by the addition of 0.2 ml of acetic acid
2. customVolatile material was removed under reduced pressure
3. customthe residue chromatographed on 300 g of silica gel eluting with methylene chloride (CH2Cl2)
4. customFractions of approximately 17 ml were collected
5. customthe solvent evaporated