Resorcinol → HCID 10925060, compound

HRID 1619167Notes

Reaction equation

HRID 1619167 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]([OH:24])[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[O:24][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]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 11430Potassium CarbonateHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate

Product 1

HCID 10925060HCID 10925060, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate (0.5 g, 1.7 mmol) and 3-hydroxyphenol (0.2 g, 2.1 mmol) in 20 mL of acetonitrile (CH3CN) was added potassium carbonate (0.35 g, 2.6 mmol). The reaction mixture was stirred under reflux and concentrated in a vacuum to remove the solvent. The residue was stirred in water (20 mL) and the aqueous layer was extracted twice with 20 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated in a vacuum to remove the solvent. The concentrate was purified by silica gel chromatography to afford (E)-methyl 2-(2-((3-hydroxyphenoxy)methyl)phenyl)-3-methoxyacrylate as a white solid (0.4 g, yield 74%).

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated in a vacuum
  3. customto remove the solvent
  4. stirringThe residue was stirred in water (20 mL)
  5. extractionthe aqueous layer was extracted twice with 20 mL of dichloromethane
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in a vacuum
  8. customto remove the solvent
  9. customThe concentrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-56006303c5814305825516104f211c52
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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