Nitric Acid → HCID 23031109, compound

HRID 1766642Notes

Reaction equation

HRID 1766642 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[OH:11].O.[N+:13]([O-])([OH:15])=[O:14].S([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[I:1][C:2]1[CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[OH:11]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962Water2×HCID 24437Sodium SulfiteHCID 23031206HCID 23031206, compound

Product 1

HCID 23031109HCID 23031109, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-iodoindan-4-ol (358 mg) in acetic acid (3 mL) was added water (0.5 mL). To the solution was added nitric acid (60%, 0.105 mL) in small portions under ice-cooling, and the mixture was stirred under ice-cooling for 20 min. After adding water (10 mL) and aqueous sodium sulfite (1.5 g/10 mL) successively, the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated sodium hydrogen carbonate and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was crystallized from a small amount of dichloromethane and hexane to give the title compound (70 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 20 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water, saturated sodium hydrogen carbonate and brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was crystallized from a small amount of dichloromethane and hexane

Sources & evidence

ORD record
ord-d1b00def53f04a36aa10fbc94963b9a5
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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