3-Hydroxybenzaldehyde → HCID 14857823, compound

HRID 1619169Notes

Reaction equation

HRID 1619169 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11].[OH:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=[O:22].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH:21]([C:20]1[CH:19]=[C:18]([CH:25]=[CH:24][CH:23]=1)[O:17][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11])=[O:22]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate

Product 1

HCID 14857823HCID 14857823, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate (3.0 g, 10.52 mmol), 3-hydroxybenzaldehyde (1.41 g, 1.1 eq) and potassium carbonate (3.0 g, 3.0 eq) in a mixture of acetonitrile (CH3CN, 30 mL)/H2O (5 mL) was refluxed for 15 hours. After concentration in a vacuum to remove the reaction solvent, the residue was stirred in water (50 mL) and the aqueous layer was extracted twice with 50 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in a vacuum to remove the solvent. Purification by silica gel chromatography afforded (E)-methyl 2-(2((3-formylphenoxy)methyl)phenyl)-3-methoxyacrylate as a white solid (3.0 g, yield 87%).

Workup

  1. temperaturewas refluxed for 15 hours
  2. concentrationAfter concentration in a vacuum
  3. customto remove the reaction solvent
  4. extractionthe aqueous layer was extracted twice with 50 mL of dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in a vacuum
  8. customto remove the solvent
  9. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-7e39db153a034c9dac9e592a10b54aca
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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