m-Chloroperbenzoic acid → HCID 86745023, compound

HRID 2249208Notes

Reaction equation

HRID 2249208 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[CH3:9][O:10][C:11]1[CH:17]=[C:16]([OH:18])[C:15]([CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[CH:14][C:12]=1[OH:13].ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[O:32]1[C:21]([CH3:23])([CH3:22])[CH:20]1[CH2:19][C:15]1[C:16]([OH:18])=[CH:17][C:11]([O:10][CH3:9])=[C:12]([CH:14]=1)[OH:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86745022HCID 86745022, compound

Product 1

HCID 86745023HCID 86745023, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 2-methoxy-5-(3-methyl-2-butenyl)hydroquinone diacetate (2.84 g) in dichloromethane (40 ml) was added m-chloroperbenzoic acid (2.09 g, 80% purity) in several portions at 5° C. After the addition, the mixture was stirred for one hour at 5° C., washed twice with a mixture of aqueous sodium bicarbonate solution and aqueous sodium thiosulfinate solution, dried, and concentrated in vacuo. The residue was crystallized from n-hexane to give 5-(2,3-epoxy-3-methylbutyl)-2-methoxyhydroquinone diacetate as a white solid (2.93 g).

Workup

  1. additionAfter the addition
  2. washwashed twice with a mixture of aqueous sodium bicarbonate solution and aqueous sodium thiosulfinate solution
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-bd65eb4a9f974a7d8fef2368e1b47585
Source dataset
uspto-grants-1991_08
Patent number
US05043354

Reaction notes

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