Methyl iodide → 4-Tert-butyl-1-methoxy-2-methylbenzene

HRID 406352Notes

Reaction equation

HRID 406352 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.[C:9]([C:13]1[CH:18]=[CH:17][C:16](O)=[C:15]([CH3:20])[CH:14]=1)([CH3:12])([CH3:11])[CH3:10].CCCCCC>CN(C)C=O>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([O:4][CH3:1])=[C:15]([CH3:20])[CH:14]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 73794-Tert-Butyl-2-MethylphenolHCID 8058HexaneHCID 11430Potassium Carbonate

Product 1

HCID 124222644-Tert-butyl-1-methoxy-2-methylbenzeneYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (8.4 g) and methyl iodide (2.9 mL) were added to a solution of 4-tert-butyl-2-methylphenol (CAS #98-27-1, 5.0 g) in N,N-dimethylformamide (25 mL), and the mixture was stirred at room temperature for three days. Ice water and hexane were added to the reaction solution, and the organic layer was separated. The resulting organic layer was sequentially washed with water and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 5.16 g of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was sequentially washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8d08f1b332742e1b2fd5420fc4d5efc
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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