Water → 2-nitro-6,7-dihydro-5H-benzocycloheptene
Reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH:12](O)[C:6]=2[CH:5]=1)([O-:3])=[O:2].S([O-])(O)(=O)=O.[K+].O>C(OCC)(=O)C>[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
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).
Workup
- temperatureAfter cooling, to the mixture
- additionwas added
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate (200 ml)
- washThe combined organic layer was washed with brine (150 ml)
- dry with materialdried over anhydrous sodium sulfate
- customevaporated in vacuo
- customThe residue was purified by column chromatography on silica gel with a mixture of n-hexane and chloroform (1:1) as an eluent
Sources & evidence
- ORD record
- ord-f446c5a8ed9d4da7a684b5ff726c906f
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05387710
Reaction notes
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