3-Hydroxybenzaldehyde → 3-[(4-methylbenzyl)oxy]benzaldehyde

HRID 1169441Notes

Reaction equation

HRID 1169441 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 77224-Methylbenzyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 6933133-[(4-methylbenzyl)oxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 3-hydroxybenzaldehyde (5.00 g) dissolved in acetone (70 ml) were added 4-methylbenzyl chloride (6.51 ml), potassium carbonate (8.49 g) and sodium iodide (7.36 g), and the resulting mixture was heated at reflux for 24 hours and was then evaporated under reduced pressure to remove the solvent. The residue was mixed with water (200 ml) and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride was dried with anhydrous sodium sulfate, and was then evaporated under reduced pressure to remove the solvent. The thus-obtained residue was subjected to purification using column chromatography (ethyl acetate/hexane=1/10) to obtain 3-(4-methylbenzyloxy)benzaldehyde (7.86 g) as a colorless oily substance.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 24 hours
  3. customwas then evaporated under reduced pressure
  4. customto remove the solvent
  5. additionThe residue was mixed with water (200 ml)
  6. extractionwas extracted with ethyl acetate
  7. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  8. dry with materialwas dried with anhydrous sodium sulfate
  9. customwas then evaporated under reduced pressure
  10. customto remove the solvent
  11. customThe thus-obtained residue was subjected to purification

Sources & evidence

ORD record
ord-a2b121b0e42d414aa728b929e2f3d6aa
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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