Methyl iodide → 3-Methoxy-5-Methylphenol

HRID 1692616Notes

Reaction equation

HRID 1692616 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([OH:8])[CH:7]=1.[C:10]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:9][C:4]1[CH:5]=[C:6]([O:8][CH3:10])[CH:7]=[C:2]([OH:1])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10436OrcinolHCID 11430Potassium Carbonate

Product 1

HCID 766743-Methoxy-5-MethylphenolYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

1 mmol of 3,5-Dihydroxy-toluene was taken in 3 mL of acetone, and then 3 mmol of K2CO3 was added and stirred for several minutes. Then, a solution of CH3I (3 mmol) in 10 ml of acetone was added from a pressure-equalizing dropping funnel, and the reaction was monitored by TLC. Upon completion, the reaction mixture was filtered to remove K2CO3, and evaporated by a rotatory evaporator to remove acetone. The mixture was then purified by column chromatography to give 5-methyl-3-methoxy-phenol (80%).

Workup

  1. filtrationUpon completion, the reaction mixture was filtered
  2. customto remove K2CO3
  3. customevaporated by a rotatory evaporator
  4. customto remove acetone
  5. customThe mixture was then purified by column chromatography

Sources & evidence

ORD record
ord-400b531949204eabaa6a315fb2de00b0
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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