4-Hydroxybenzaldehyde → 4-[(2-methylbenzyl)oxy]benzaldehyde

HRID 1515089Notes

Reaction equation

HRID 1515089 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Br.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH3:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 6992o-Xylyl bromideHCID 10796Cesium carbonate

Product 1

HCID 27634324-[(2-methylbenzyl)oxy]benzaldehydeYield 103%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxybenzaldehyde (10.0 g, 81.9 mmol) and 2-methyl benzyl bromide (40.0 g, 98.3 mmol) were dissolved in dimethylformamide (100 mL), and cesium carbonate (18.2 g, 123 mmol) was added thereto, and then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 1 hour. Water was added to the reaction solution, and the organic matter was extracted with diethyl ether. The organic layer was washed with water and a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 60:40 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (19.2 g, yield: 103%).

Workup

  1. extractionthe organic matter was extracted with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution, then dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  6. customwas obtained
  7. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 60:40 (v/v)), whereby the objective title compound
  8. customwas obtained as a colorless oily substance (19.2 g, yield: 103%)

Sources & evidence

ORD record
ord-59ae6f86d281462fa067bc1f6676f0af
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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