Dimethylformamide → 2,4-Dimethylanisole

HRID 2205465Notes

Reaction equation

HRID 2205465 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[C:10](=O)([O-])[O-].[K+].[K+].CN(C=O)C.IC>O>[CH3:10][O:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 77712,4-DimethylphenolHCID 11430Potassium Carbonate

Product 1

HCID 812212,4-DimethylanisoleYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,4-dimethylphenol (7.5 g, 0.062 mol) and anhydrous potassium carbonate (25.4 g, 0.18 mol) were dissolved into DMF (75 mL) and then iodomethane (8.83 g, 0.062 mol) was dropped under an ice bath. The system was stirred overnight at room temperature. At the end of reaction, the reaction system was added with water and then extracted with ethyl acetate, and the organic phase was washed with saturated brine, then dried and evaporated in vacuum to obtain 7.11 g of the product (85%) by column chromatography.

Workup

  1. customAt the end of reaction
  2. extractionextracted with ethyl acetate
  3. washthe organic phase was washed with saturated brine
  4. customdried
  5. customevaporated in vacuum

Sources & evidence

ORD record
ord-dce38558c09b48a39aa97ea839f4fe7e
Source dataset
uspto-grants-2016_06
Patent number
US09371305B2

Reaction notes

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