Water → 4-[(4-Ethoxybenzyl)oxy]-2-hydroxy-3-methylbenzaldehyde

HRID 1888720

Reaction equation

HRID 1888720 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][O:11][C:8]2[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[C:9]=2[CH3:10])=[CH:21][CH:22]=1)[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 803952,4-Dihydroxy-3-methylbenzaldehydeHCID 20639711-(Chloromethyl)-4-Ethoxybenzene

Product 1

HCID 580476384-[(4-Ethoxybenzyl)oxy]-2-hydroxy-3-methylbenzaldehydeYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dihydroxy-3-methylbenzaldehyde (1.00 g, 6.57 mmol) in DMF (20 mL) were added potassium carbonate (1.36 g, 9.86 mmol) and 1-(chloromethyl)-4-ethoxybenzene (1.23 g, 7.23 mmol), and the mixture was stirred at room temperature for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed twice with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 3:2) to give the title compound (336 mg, yield 18%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed twice with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 3:2)

Sources & evidence

ORD record
ord-9f067abf59ce4bbdbac6d9a6f17f6350
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Linked notes

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