Dimethylformamide → 3,5-Dimethylanisole

HRID 2205461Notes

Reaction equation

HRID 2205461 reaction equation
[C:1]1([OH:9])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.[C:10](=O)([O-])[O-].[K+].[K+].CN(C=O)C.IC>O>[CH3:10][O:9][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 79483,5-DimethylphenolHCID 11430Potassium Carbonate

Product 1

HCID 701263,5-DimethylanisoleYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,5-xylenol (10 g, 0.082 mol) and anhydrous potassium carbonate (34 g, 0.25 mol) were added into DMF (150 mL) and then iodomethane (12.8 g, 0.090 mmol) 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 10 g of the product (90%) 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-6fbf1286bfbf4a849585b2d03d80823b
Source dataset
uspto-grants-2016_06
Patent number
US09371305B2

Reaction notes

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