Methanol → 2-Butyl-3,5-dimethylanisole

HRID 27865Notes

Reaction equation

HRID 27865 reaction equation
[CH2:1]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=1[OH:13])[CH2:2][CH2:3][CH3:4].[CH3:14]O.[OH-].[K+].CI>O>[CH2:1]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=1[O:13][CH3:14])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 202099972-Butyl-3,5-dimethylphenol

Product 1

HCID 202100342-Butyl-3,5-dimethylanisole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

83 g. of 2-butyl-3,5-dimethyl-phenol are dissolved in 225 ml. of methanol. After the addition of 60 g. of potassium hydroxide in 25 ml. of water, the solution is treated at room temperature with 34.2 g. of methyl iodide. The mixture is heated to boiling under reflux conditions for 3 hours, then cooled, diluted with water and extracted with ether. The ether extract is washed with diluted sodium hydroxide solution, dried over sodium sulfate and evaporated. There is obtained 2-butyl-3,5-dimethyl-anisole, which is purified by absorption on silica gel, using hexane/methylene chloride 70:30 parts by volume as the eluent, before processing further.

Workup

  1. additionAfter the addition of 60 g
  2. temperatureThe mixture is heated
  3. temperaturecooled
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washis washed with diluted sodium hydroxide solution
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-0bcd2d4c91404758aaea6ef8d06ddf79
Source dataset
uspto-grants-1980_09
Patent number
US04224244

Reaction notes

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