Methyl iodide → 2-Isopropylanisole

HRID 1392549Notes

Reaction equation

HRID 1392549 reaction equation
[OH-].[K+].[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])([CH3:5])[CH3:4].CI.[CH3:15]CN(CC)CC>O.C(Cl)Cl>[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:15])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 69432-IsopropylphenolHCID 8471TriethylamineHCID 14797Potassium Hydroxide

Product 1

HCID 2706232-IsopropylanisoleYield 313.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred 20° C. solution comprised of KOH (1154 g, 4.75 mol), Bu4N+ HSO4− (140 g, 0.41 mol) in H2O (5.6 L) was added commercially available 2-isopropylphenol (590 g, 4.33 mol) in CH2Cl2 (5.6 L). After 30 min, MeI (741 g, 5.22 mol) was added prior to stirring the reaction overnight. After separation of the layers, Et3N (185 mL, 1.3 mol) was added to the CH2Cl2 fraction to destroy the residual MeI. After 15 min, the CH2Cl2 was removed under vacuum and the salts suspended in cyclohexane (4 L) prior to filtration. The cyclohexane filtrate was sequentially washed with 2N HCl followed by 2 brine washes. Concentration under vacuum yielded 2-isopropylanisole (612 g, 94%) as a light yellow oil.

Workup

  1. customTo a stirred 20° C.
  2. customthe reaction overnight
  3. customto destroy the residual MeI
  4. waitAfter 15 min
  5. customthe CH2Cl2 was removed under vacuum
  6. filtrationto filtration
  7. washThe cyclohexane filtrate was sequentially washed with 2N HCl
  8. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-020beb5f3d43468a882780311157c50c
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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