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

HRID 2185039Notes

Reaction equation

HRID 2185039 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-52ce2843323e43f18ff568c5caf9e4bf
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

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