Nitric Acid → HCID 22400281, compound
Reaction equation
[CH2:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([OH:10])[C:4]=2[CH2:3][CH2:2]1.[N+:11]([O-])([OH:13])=[O:12]>C(O)(=O)C>[OH:10][C:5]1[C:4]2[CH:3]=[CH:2][CH2:1][C:9]=2[CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The starting material, 4-indanol (i.e., Formula 5) is dissolved in an organic acid, preferably glacial acetic acid, at a temperature in the range of about 20°-30° C., preferably about room temperature. To this solution is added in a gradual manner a solution of concentrated nitric acid (about 1 to 2 molar equivalents, preferably about 1.5 molar equivalents) in an organic acid, preferably glacial acetic acid. The reaction mixture is stirred for a period of about 15 minutes to 1 hour, preferably about 30 minutes, at a temperature in the range of 20°-30° C., preferably about room temperature. When the reaction is substantially complete, the 4-hydroxy-5-nitrobenzocyclopentene of Formula 6 is isolated and purified by conventional means, preferably by flash column chromatography.
Sources & evidence
- ORD record
- ord-1b5a48fe13ac4d87b2bd75c7f6162a20
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05530005
Reaction notes
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