O-Cresol → 2-Methylanisole

HRID 2205463Notes

Reaction equation

HRID 2205463 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][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][CH:3]=[CH:2][C:1]=1[CH3:8]

Participants

6

Reactant 4

HCID 335O-CresolHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 336372-MethylanisoleYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

o-cresol (3.0 g, 0.028 mol) and anhydrous potassium carbonate (7.7 g, 0.056 mol) were dissolved into 50 ml of DMF and then iodomethane (3.9 g, 0.028 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 3 g of the product (89%) 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-281f3a47488f4b0da6f2de1afe00f3c7
Source dataset
uspto-grants-2016_06
Patent number
US09371305B2

Reaction notes

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