Methyl iodide → HCID 58396979, compound

HRID 1361612Notes

Reaction equation

HRID 1361612 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH2:11][CH3:12])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[OH:13].[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.CCOC(C)=O>[CH3:14][NH:1][C:2]1[CH:7]=[C:6]([C:8]([CH2:11][CH3:12])([CH3:9])[CH3:10])[CH:5]=[CH:4][C:3]=1[OH:13]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3300422-Amino-4-tert-amylphenol

Product 1

HCID 58396979HCID 58396979, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-tert-pentylphenol (5.00 g, 27.8 mmol) and potassium carbonate (3.88 g, 28.1 mmol) were mixed at RT for 2.5 hours in DMF (15 mL). Methyl iodide (1.20 mL, 19.3 mmol) was added and the mixture was stirred overnight at RT. Diluted the mixture with EtOAc and extracted with aqueous sodium bicarbonate and water. Dried the organic layers over sodium sulfate, filtered, concentrated and purified by silica gel chromatography (10-15% MTBE/hexanes). Concentrated the product fractions to yield the title compound.

Workup

  1. extractionextracted with aqueous sodium bicarbonate and water
  2. dry with materialDried the organic layers over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (10-15% MTBE/hexanes)
  6. concentrationConcentrated the product fractions

Sources & evidence

ORD record
ord-ed576fc682824fb0a171f0b15434cda1
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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