m-Chloroperbenzoic acid → 2,5-Dimethoxy-3,4,6-trimethylphenol

HRID 1742481Notes

Reaction equation

HRID 1742481 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([O:21][CH3:22])=[C:16]([CH3:23])[C:15]=1[CH3:24]>C(Cl)Cl>[CH3:12][O:13][C:14]1[C:15]([CH3:24])=[C:16]([CH3:23])[C:17]([O:21][CH3:22])=[C:18]([CH3:20])[C:19]=1[OH:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 109240691,4-Dimethoxy-2,3,5-trimethyl-benzene

Product 1

HCID 190092542,5-Dimethoxy-3,4,6-trimethylphenolYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9.4 g of m-chloroperbenzoic acid (70% purity) in 100 ml of methylene chloride was added dropwise, whilst ice-cooling, to a solution of 4.6 g of 1,4-dimethoxy-2,3,5-trimethylbenzene in 20 ml of methylene chloride, and the resulting mixture was stirred at the same temperature for 30 minutes and then at room temperature for 5 hours. At the end of this time, the reaction mixture was washed with a 5% w/v aqueous solution of sodium hydrogensulfite, with a 5% w/v aqueous solution of sodium hydrogencarbonate and with water, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was then removed from the reaction mixture by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using benzene and a 50:1 by volume mixture of benzene and ethyl acetate as the eluents, to give 1.3 g of the title compound.

Workup

  1. waitat room temperature for 5 hours
  2. washAt the end of this time, the reaction mixture was washed with a 5% w/v aqueous solution of sodium hydrogensulfite, with a 5% w/v aqueous solution of sodium hydrogencarbonate and with water, in that order
  3. dry with materialafter which it was dried over anhydrous sodium sulfate
  4. customThe solvent was then removed from the reaction mixture by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additiona 50:1 by volume mixture of benzene and ethyl acetate as the eluents

Sources & evidence

ORD record
ord-6340467fb38946c58b6a30f0416c965d
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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