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

HRID 1172807Notes

Reaction equation

HRID 1172807 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2C=O)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:25])C=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:12]([OH:25])=[CH:11][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 27676752-(4-chlorophenoxy)benzaldehyde

Product 1

HCID 123461204-(4-Chlorophenoxy)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude aldehyde from step 1 (23.3 g, 0.10 mmol) was dissolved in dichloromethane (500 mL), and m-chloroperbenzoic acid (70%, 50.0 g, 0.20 mmol) and sodium bicarbonate (25.2 g, 0.30 mmol) were added. The resulting heterogeneous mixture was stirred and heated under reflux for 2 h and then quenched with an aqueous solution of sodium sulfite (0.5 M, 500 mL). After stirring at 25° C. for 30 min, the organic phase was separated and the aqueouse phase was extracted with dichloromethane (2×200 mL). The combined organic phases were washed with a saturated solution of sodium bicarbonate (2×200 mL), dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel, eluting with an 8:2 mixture of hexane and ethyl acetate to give the title phenol.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 h
  3. customquenched with an aqueous solution of sodium sulfite (0.5 M, 500 mL)
  4. stirringAfter stirring at 25° C. for 30 min
  5. customthe organic phase was separated
  6. extractionthe aqueouse phase was extracted with dichloromethane (2×200 mL)
  7. washThe combined organic phases were washed with a saturated solution of sodium bicarbonate (2×200 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel
  11. washeluting with an 8:2 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-a7609a2c0e894ae69e3c8b6a2de92cba
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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