Реакция #361245

Уравнение реакции

3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol

potassium hydrogensulfate

water

→

2-nitro-6,7-dihydro-5H-benzocycloheptene

Выход 74.5%

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling, to the mixture
2. 2
   workup.ADDITIONwas added
3. 3
   ДругоеThe organic layer was separated
4. 4
   Экстракцияthe aqueous layer was extracted with ethyl acetate (200 ml)
5. 5
   ПромывкаThe combined organic layer was washed with brine (150 ml)
6. 6
   Сушкаdried over anhydrous sodium sulfate
7. 7
   Другоеevaporated in vacuo
8. 8
   ДругоеThe residue was purified by column chromatography on silica gel with a mixture of n-hexane and chloroform (1:1) as an eluent

Методика

A mixture of 3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (70.67 g) and potassium hydrogensulfate (53.00 g) was heated at 160° C. for 1 hour. After cooling, to the mixture was added a mixture of water (400 ml) and ethyl acetate (400 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (200 ml). The combined organic layer was washed with brine (150 ml), dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of n-hexane and chloroform (1:1) as an eluent to give 2-nitro-6,7-dihydro-5H-benzocycloheptene (48.1 g).

Источник