4-Methoxyphenol → 4-(4-Methoxyphenoxy)benzaldehyde

HRID 1586091Notes

Reaction equation

HRID 1586091 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 707414-Bromobenzaldehyde

Product 1

HCID 104895194-(4-Methoxyphenoxy)benzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-methoxyphenol (1.0 g, 0.00806 mol), 4-bromobenzaldehyde (1.49 g, 0.00805 mol), CuO (0.64 g, 0.00805 mol), potassium carbonate (1.11 g, 0.00803 mol) in pyridine (100 mL) was refluxed for 60 h. The reaction mixture was filtered into ice/water and the product was extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO4), concentrated and chromatographed with CH2Cl2 to afford 1.56 g (85%) of 4-(4-methoxyphenoxy)benzaldehyde.

Workup

  1. temperaturewas refluxed for 60 h
  2. filtrationThe reaction mixture was filtered into ice/water
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customchromatographed with CH2Cl2

Sources & evidence

ORD record
ord-5241f8d49ba34ccbafa6ce360080a7f6
Source dataset
uspto-grants-1999_08
Patent number
US05942532

Reaction notes

Loading…