Peracetic Acid → HCID 21509017, compound

HRID 1287513Notes

Reaction equation

C[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].C([O-])(=[O:26])C.[Na+].C(OO)(=O)C>ClCCl>[Cl:15][C:6]1[C:7]2[O:14][CH:12]([CH2:13][OH:26])[CH2:11][C:8]=2[C:9]2[CH2:10][CH:2]([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

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-methyl-2-phenyl-4-allyl-5-hydroxy-6,7-dichloro-1-indanone (8.2 g., 0.024 mole) in dichloromethane (80 ml.) is added sodium acetate (150 mg.) and 40% peracetic acid (6 ml.). The reaction is stirred at 25°C. for 12 days during which time two 1 ml. portions of 40% peracetic acid are added at four day intervals. The reaction mixture 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 20 minutes affording 4,5-dichloro-2-hydroxymethyl-6-oxo-7-phenyl-1,2,7,8-tetrahydro-6H-indeno-[5,4-b]-furan (α-isomer) which is used in the next step without further purification.

Workup

washThe reaction mixture is washed with water, aqueous sodium bicarbonate and brine
distillationThe solvent is distilled at reduced pressure

Sources & evidence

ORD record: ord-8edb28041ce6432287863d07b594a6fc
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03984552

Reaction notes

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