Methanol → 3-Methoxy-1,2,4,5-tetramethylbenzene

HRID 1164285Notes

Reaction equation

HRID 1164285 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[C:4]([CH3:10])[C:3]=1[OH:11].[CH3:12]I.[H-].[Na+].CO>CS(C)=O.CCOCC.O>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[C:4]([CH3:10])[C:3]=1[O:11][CH3:12]

Participants

8

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 106942,3,5,6-TetramethylphenolHCID 24758Sodium hydride2×

Product 1

HCID 2786643-Methoxy-1,2,4,5-tetramethylbenzene

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

In 150 ml of DMSO were dissolved 15.0 g of 2,3,5,6-tetramethylphenol and 28 ml of methyl iodide. Under ice-cooling 6.3 g of 60% sodium hydride in oil was added, and the mixture was stirred at room temperature for 1 hour. The excess sodium hydride was decomposed with MeOH and after addition of water extraction with ether was carried out. The extract was dried over sodium sulfate. Removal of the solvent by distillation leaves crystals which were recrystallized from MeOH.

Workup

  1. additionwas added
  2. dry with materialThe extract was dried over sodium sulfate
  3. customRemoval of the solvent
  4. distillationby distillation
  5. customleaves crystals which
  6. customwere recrystallized from MeOH

Sources & evidence

ORD record
ord-655501f6e8924ea0b35aba1e4c8912f1
Source dataset
uspto-grants-1983_01
Patent number
US04368150

Reaction notes

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