Реакция #76415

Уравнение реакции

sodium nitrite

Methyl nitrite

sodium hydroxide

4-{4-[4-(3-cyano-propenyl)-benzyl]-phenyl}-but-3-enenitrile

→

4-{4-[4-(3-cyano-3-hydroxyimino-propenyl)-benzyl]-phenyl}-2-hydroxyimino-but-3-enenitrile

Выход 76.0%

Растворители

methanol

methanol

Условия реакции

Обработка

1. 1
   Другоеprepared
2. 2
   Другоеis bubbled through the suspension at 2° C. for 25 min
3. 3
   ДругоеThe solvent is then evaporated
4. 4
   workup.DISSOLUTIONthe residue is dissolved in 200 ml of water
5. 5
   Экстракцияextracted with toluene (the extract
6. 6
   Промывкаwashed neutral with water
7. 7
   Сушкаdried (MgSO4)
8. 8
   Концентрированиеconcentrated by evaporation

Методика

A solution of sodium hydroxide (0.8 g; 0.02 mol) in 30 ml of methanol is added to a suspension of 4-{4-[4-(3-cyano-propenyl)-benzyl]-phenyl}-but-3-enenitrile (3.0 g; 0.01 mol), prepared as described in example 6.2, in 20 ml of methanol. Methyl nitrite, generated from 2.07 g (0.03 mol) of sodium nitrite as described in example 2.2, is bubbled through the suspension at 2° C. for 25 min, and the mixture is then left at room temperature for 48 h. The solvent is then evaporated, the residue is dissolved in 200 ml of water, extracted with toluene (the extract is discarded), and acidified with conc. hydrochloric acid. The beige precipitate is taken up in ethyl acetate, washed neutral with water, dried (MgSO4) and concentrated by evaporation. 2.7 g (76%) of 4-{4-[4-(3-cyano-3-hydroxyimino-propenyl)-benzyl]-phenyl}-2-hydroxyimino-but-3-enenitrile are obtained as a light brown solid, melting point 142-145° C. (dec).

Источник