Methyl iodide → 2-Isopropylanisole

HRID 1418762Notes

Reaction equation

HRID 1418762 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].CI.[C:13](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOCC>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:13])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 69432-IsopropylphenolHCID 11430Potassium Carbonate

Product 1

HCID 2706232-IsopropylanisoleYield 93.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-isopropylphenol (1) (12.0 g, 88.1 mmol), methyl iodide (25.0 g, 176.2 mmol), and potassium carbonate (24.3 g, 176.2 mmol) in 44 mL of DMF was stirred for 20 hours at room temperature. The reaction mixture was diluted with 300 mL of ether and washed with 250 mL of water and 5×100 mL of brine. The organic portion was dried (MgSO4), filtered, and evaporated to give an oil, which was purified by flash column chromatography (silica gel, 90:10 hexane/ethylacetate) to give 2-isopropylanisole (2) (12.5 g, 82.1 mmol, 93%); 1HNMR (CDCl3) δ 1.2 (d, 6H), 3.3 (heptet, 1H), 3.8 (s, 3H), 6.8 (d, 1H), 6.88 (t, 1H), 7.13 (d, 1H), 7.2 (t, 1H).

Workup

  1. washwashed with 250 mL of water and 5×100 mL of brine
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil, which
  6. customwas purified by flash column chromatography (silica gel, 90:10 hexane/ethylacetate)

Sources & evidence

ORD record
ord-f354f42ea0414d8396c6a78565c71727
Source dataset
uspto-grants-1999_03
Patent number
US05883294

Reaction notes

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