m-Chloroperbenzoic acid → Bicyclo[4.2.0]octa-1,3,5-trien-7-ol

HRID 893045Notes

Reaction equation

HRID 893045 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]O)=O.[C:12]1(C=O)C2C=CC=CC=2C=1.[F-].[K+]>C(Cl)Cl>[OH:7][CH:5]1[C:4]2=[CH:9][CH:10]=[CH:11][CH:2]=[C:3]2[CH2:12]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 522689Potassium FluorideHCID 18965788HCID 18965788, compound

Product 1

HCID 562415Bicyclo[4.2.0]octa-1,3,5-trien-7-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Chloroperoxybenzoic acid (0.66 g) was added to a solution of benzocyclobutene aldehyde (0.2 g) in methylene chloride (10 mL) at 0° C. The mixture was stirred for 30 minutes at 0° C. and then warmed to room temperature. Stirring was continued for 12 hours at room temperature. Potassium floride (0.3 g) was added and stirring continued for an additional two hours. The reaction mixture was filtered, washed with sodium bisulfite solution and the solvent was removed by flash column chromatography. Liquid chromatographic analysis found a yield to hydroxy benzocyclobutene of approximately 55 percent and no benzocyclobutene carboxylic acid, with the balance comprising unidentified materials characterized as undesired product.

Workup

  1. temperaturewarmed to room temperature
  2. stirringStirring
  3. waitwas continued for 12 hours at room temperature
  4. stirringstirring
  5. waitcontinued for an additional two hours
  6. filtrationThe reaction mixture was filtered
  7. washwashed with sodium bisulfite solution
  8. customthe solvent was removed by flash column chromatography

Sources & evidence

ORD record
ord-b684eed9054641449ac96551555fa824
Source dataset
uspto-grants-1992_06
Patent number
US05120884

Reaction notes

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