P-Cresol → 4-Methylanisole

HRID 2205466Notes

Reaction equation

HRID 2205466 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[C:9](=O)([O-])[O-].[K+].[K+].CN(C=O)C.IC>O>[CH3:9][O:7][C:6]1[CH:5]=[CH:4][C:3]([CH3:8])=[CH:2][CH:1]=1

Participants

6

Reactant 4

HCID 2879P-CresolHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 77314-MethylanisoleYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-cresol (20 g, 0.19 mol) and anhydrous potassium carbonate (75 g, 0.54 mol) were added into DMF (500 mL) and then iodomethane (27 g, 0.19 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 20 g of the product (86%) 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-cdfee3ab1c9646458e288a0f56697d5a
Source dataset
uspto-grants-2016_06
Patent number
US09371305B2

Reaction notes

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