Methyl iodide → 2-Isopropylanisole

HRID 1872418Notes

Reaction equation

HRID 1872418 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-Isopropylanisole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-isopropylphenol (a compound of Formula 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 (a compound of Formula 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-0df337191d734b0e9f16f557d5429b1f
Source dataset
uspto-grants-2000_08
Patent number
US06107517

Reaction notes

Loading…