反应详情

A solution of 26.4 g. (0.1 mol.) of (±)-6-acetoxy-2-hydroxy-2,5,7,8 -tetramethylchroman in 200 ml. of dimethylsulfoxide was rapidly stirred as 32.5 g. (0.5 mol.) of granular KCN was added by sifting so that a uniformly dispersed suspension was obtained. The resulting mixture was cooled to 15° centigrade as 47.0 ml. of 12N aqueous H 2 SO 4 was added over 1.25 hours as the internal temp. was maintained at 20° centigrade. Tlc at this point showed a major, slower-running spot in addition to traces of starting material. The material was poured into diethylether and H 2 O. The ether solutions were washed with water and brine, dried over NaSO4 and stripped of solvent to yield (±)-2-cyano-4-(5-acetoxy-2-hydroxy-3,4,6-trimethylphenyl) butan-2-ol as a gum.

1. filtrationby sifting so that a uniformly dispersed suspension
2. customwas obtained
3. temperatureThe resulting mixture was cooled to 15° centigrade as 47.0 ml
4. additionof 12N aqueous H 2 SO 4 was added over 1.25 hours as the internal temp
5. temperaturewas maintained at 20° centigrade
6. additionin addition to traces of starting material
7. washThe ether solutions were washed with water and brine
8. dry with materialdried over NaSO4