Toluene → 3-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

HRID 2299651Notes

Reaction equation

HRID 2299651 reaction equation
N[C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.N([O-])=[O:15].[Na+].S([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>S(=O)(=O)(O)O>[OH:15][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 24437Sodium SulfiteHCID 2668073-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-oneHCID 23668193Sodium Nitrite

Product 1

HCID 2295073-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-oneYield 56.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 3-amino-6,7,8,9-tetrahydrobenzocyclohepten-5-one (12.53 g) in 10% sulfuric acid (130 ml) was added sodium nitrite (4.9 g) and sodium sulfite (694 mg) under ice-cooling. After being stirred for 20 minutes at this temperature, to the reaction mixture was added toluene (100 ml), stirred at the room temperature for 18 hours and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to afford 3-hydroxy-6,7,8,9-tetrahydrobenzocyclohepten-5-one (7.08 g).

Workup

  1. temperaturecooling
  2. stirringstirred at the room temperature for 18 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-2b6bd11869b445898eb62a4d2c830ab6
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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