3-Hydroxybenzaldehyde → HCID 14857823, compound

HRID 1619171Notes

Reaction equation

HRID 1619171 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

(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) were together refluxed for 15 hours in acetonitrile (CH3CN, 30 mL)/H2O (5 mL). Concentration at a reduced pressure removed 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. The concentrate was purified by silica gel chromatography to give (E)-methyl 2-(2((3-formylphenoxy)methyl)phenyl)-3-methoxyacrylate as a white solid (3.0 g, yield 87%).

Workup

  1. concentrationConcentration at a reduced pressure
  2. customremoved the reaction solvent
  3. extractionthe aqueous layer was extracted twice with 50 mL of dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in a vacuum
  7. customto remove the solvent
  8. customThe concentrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9e7795ef2ec44aa48bb2de825c8bf5d1
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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