2,5-Dimethylphenol → (E)-2-(2-((2,5-dimethyl phenoxy)methyl phenyl))-3-methoxy acrylic acid methyl ester

HRID 1619175Notes

Reaction equation

HRID 1619175 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].[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[OH:25].[OH-].[K+]>C(#N)C>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[O:25][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 72672,5-DimethylphenolHCID 14797Potassium HydroxideHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate

Product 1

HCID 11631236(E)-2-(2-((2,5-dimethyl phenoxy)methyl phenyl))-3-methoxy acrylic acid methyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate (20 g, 70.1 mmol) was reacted with 2,5-dimethylphenol (8.56 g, 1.0 eq) in 400 mL of acetonitrile (CH3CN) in the presence of potassium hydroxide (4.65 g, 1.1 eq) at room temperature for 4 hours, followed by removing the reaction solvent by concentration in a vacuum. The residue was stirred in water (200 mL) and the aqueous layer was extracted twice with 200 mL of dichloromethane. The organic layer thus obtained was dried over anhydrous magnesium sulfate, filtered and concentrated in a vacuum to remove the solvent. The residue was purified using silica gel chromatography to give (E)-methyl 2-(2-((2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate as a white solid (18.5 g, yield 81%).

Workup

  1. customby removing the reaction solvent
  2. concentrationby concentration in a vacuum
  3. extractionthe aqueous layer was extracted twice with 200 mL of dichloromethane
  4. customThe organic layer thus obtained
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in a vacuum
  8. customto remove the solvent
  9. customThe residue was purified

Sources & evidence

ORD record
ord-75fc4cfbd6844ffd87ad09b236d70be4
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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