Methanol → 2-Butyl-3,5-dimethylanisole

HRID 542352Notes

Reaction equation

HRID 542352 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-0c0f935aa45f4ac7b65d1a6ee2f036f8
Source dataset
uspto-grants-1987_04
Patent number
US04656310

Reaction notes

Loading…