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

HRID 2288884Notes

Reaction equation

HRID 2288884 reaction equation
[F: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>[F: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 38568024-(4-Fluorophenoxy)benzaldehyde

Product 1

HCID 129406244-(4-Fluorophenoxy)phenol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-(4-fluorophenoxy)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 the title compound.

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-873d5c5f077449ebb6fee600f8ab9f4a
Source dataset
uspto-grants-2000_07
Patent number
US06090839

Reaction notes

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