m-Chloroperbenzoic acid → HCID 12741923, compound

HRID 1287519Notes

Reaction equation

HRID 1287519 reaction equation
[CH3:1][C:2]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][C:9]2[C:4](=[C:5]([Cl:16])[C:6]([Cl:15])=[C:7]([OH:14])[C:8]=2[CH2:11][CH:12]=[CH2:13])[C:3]1=[O:17].ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)Cl>[Cl:15][C:6]1[C:7]2[O:14][CH:12]([CH2:13][OH:32])[CH2:11][C:8]=2[C:9]2[CH2:10][C:2]([CH3:1])([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:3](=[O:17])[C:4]=2[C:5]=1[Cl:16]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12741919HCID 12741919, compound

Product 1

HCID 12741923HCID 12741923, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-methyl-2-phenyl-4-allyl-5-hydroxy-6,7-dichloro-1-indanone (1.73 g., 0.005 mole) in methylene chloride (30 ml.) is added m-chloroperbenzoic acid (1.03 g., 0.006 mole) and 4,4'-thiobis-6-tert-butyl-m-cresol (10 mg.). The reaction is heated at reflux for 5 hours then cooled to 25°C. The m-chlorobenzoic acid which separates is filtered and the solution is washed with water, aqueous sodium bicarbonate and brine. The solvent is distilled at reduced pressure and the residual oil is heated at 120°C. for twenty minutes affording 4,5-dichloro-2-hydroxymethyl-6-oxo-7-methyl-7-phenyl-1,2,7,8-tetrahydro-6H-indeno[5,4-b]-furan (β-isomer) which is used in the next step without further purification.

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 5 hours
  3. filtrationThe m-chlorobenzoic acid which separates is filtered
  4. washthe solution is washed with water, aqueous sodium bicarbonate and brine
  5. distillationThe solvent is distilled at reduced pressure
  6. temperaturethe residual oil is heated at 120°C. for twenty minutes

Sources & evidence

ORD record
ord-53ade46a84b7496992ebb7158d91f9f8
Source dataset
uspto-grants-1976_10
Patent number
US03984552

Reaction notes

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