m-Chloroperbenzoic acid → 4-(4-Methylphenoxy)phenol

HRID 613408Notes

Reaction equation

HRID 613408 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10](C=O)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([OH:25])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 47392074-(4-Methylphenoxy)benzaldehyde

Product 1

HCID 6414404-(4-Methylphenoxy)phenol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-(4'-methylphenoxy)benzaldehyde (9.00 g, 41.63 mmol) in CHCl3 (75 mL) was treated with m-chloroperbenzoic acid (46-85%, 15.80 g, 52.00 mmol) and stirred for 3 h at room temperature. The reaction was washed with sat. aq. NaHSO3, sat. aq. NaHCO3, and water. The organic layer is concentrated and the residual oil taken up in MeOH (10 mL) containing a few drops of conc. HCL and stirred for 1 h at room temperature. The solvent is removed in vacuo and the resulting oil was chromatographed on silica gel (20% ethyl acetate/hexane) to afford 4-(4'-methylphenoxy)phenol.

Workup

  1. washThe reaction was washed with sat. aq. NaHSO3, sat. aq. NaHCO3, and water
  2. concentrationThe organic layer is concentrated
  3. additioncontaining a few drops of conc. HCL
  4. stirringstirred for 1 h at room temperature
  5. customThe solvent is removed in vacuo
  6. customthe resulting oil was chromatographed on silica gel (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c44d678a2596438fa1bc71df2fd88669
Source dataset
uspto-grants-1999_12
Patent number
US06008237

Reaction notes

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