Isopropyl iodide → 3-Isopropoxy-N,N-dimethylaniline

HRID 215928

Reaction equation

HRID 215928 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+].I[CH:18]([CH3:20])[CH3:19]>CC(C)=O>[CH:18]([O:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[N:2]([CH3:10])[CH3:1])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 74213-(Dimethylamino)phenolHCID 11430Potassium Carbonate

Product 1

HCID 580062633-Isopropoxy-N,N-dimethylaniline

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-(dimethylamino)phenol (2.0 g, 14.60 mmol) in acetone (40.0 mL) were added K2CO3 (20.2 g, 146.0 mmol) and 2-iodopropane (2.20 mL, 21.90 mmol), and the reaction was refluxed for 18 h, then cooled to room temperature, and filtered through Celite. The solvent was removed under vacuum, and the residue was purified by silica gel chromatography using ethyl acetate (20%) and hexanes (80%) as eluent to produce Compound 135 as yellow oil.

Workup

  1. temperaturethe reaction was refluxed for 18 h
  2. filtrationfiltered through Celite
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-56a13a33a481464abc3dc54c25c3545e
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Linked notes

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