Methyl iodide → 1-Isopropyl-3-methoxy-benzene

HRID 51806Notes

Reaction equation

HRID 51806 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[C:11]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 120593-Isopropylphenol

Product 1

HCID 109316061-Isopropyl-3-methoxy-benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-isopropyl-phenol (5.00 g, 36.2 mmols) in 50 mL of acetone was added K2CO3 (7.50 g, 54.3 mmols) and iodomethane (10.3 g, 72.5 mmols). The resulting solution was heated to 50° C. and stirred for 18 hours, cooled to room temperature, and concentrated under reduced pressure. The residual oil was dissolved in Et2O and washed with H2O, saturated aqueous NaHCO3, and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The crude methyl ether was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residual oil was dissolved in Et2O
  4. washwashed with H2O, saturated aqueous NaHCO3, and saturated aqueous NaCl
  5. dry with materialbefore being dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude methyl ether was used without further purification

Sources & evidence

ORD record
ord-56f70b1f6ce1494888a9e402c0731e7c
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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