Potassium Iodide → 1-Butanol, 4-(methylphenylamino)-

HRID 2248833Notes

Reaction equation

HRID 2248833 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[I-].[K+].C(=O)(O)[O-].[Na+]>CS(C)=O.O>[OH:14][CH2:13][CH2:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7515N-MethylanilineHCID 1183884-BromobutanolHCID 516892Sodium Bicarbonate

Product 1

HCID 100581051-Butanol, 4-(methylphenylamino)-

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A stirred solution of 107.2 g (1 mole) of N-methylaniline, 153.0 g (1 mole) of 4-bromo-1-butanol, 166 g (1 mole) of potassium iodide, and 168 g (2 mole) of sodium bicarbonate in dimethylsulfoxide is heated at 90° C. until the reaction is complete as indicated by thin layer chromatography. After cooling to room temperature, the reaction mixture is poured into a four-fold excess of water, and the aqueous solution is extracted with methylene chloride. The solvent is removed in vacuo, and the residual product is dissolved in a small amount of methylene chloride and swirled with silica gel. After removal of the silica gel, the solution is filtered through cotton and evaporated to yield compound A.

Workup

  1. extractionthe aqueous solution is extracted with methylene chloride
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residual product is dissolved in a small amount of methylene chloride
  4. customAfter removal of the silica gel
  5. filtrationthe solution is filtered through cotton
  6. customevaporated

Sources & evidence

ORD record
ord-293062daa9384489ac47621fe4ecf46a
Source dataset
uspto-grants-1991_08
Patent number
US05041510

Reaction notes

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