4-Aminophenol → m-aminophenoxy-2-methylpropyl Methyldimethoxysilane

HRID 236629Notes

Reaction equation

HRID 236629 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3](O)[CH:2]=1.[OH-:9].[Na+].CS(C)=O.[CH3:15][CH:16]([CH2:24]Cl)[CH2:17][Si:18]([CH3:23])([O:21][CH3:22])[O:19][CH3:20]>C1(C)C=CC=CC=1>[NH2:7][C:6]1[CH:1]=[C:2]([CH:3]=[CH:4][CH:5]=1)[O:9][CH2:20][O:19][Si:18]([CH2:17][CH:16]([CH3:24])[CH3:15])([CH3:23])[O:21][CH3:22]

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 86684(3-Chloro-2-methylpropyl)dimethoxymethylsilane

Product 1

HCID 70443251m-aminophenoxy-2-methylpropyl Methyldimethoxysilane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

Using the general procedure described in Example 1 a reactor is charged with 60 g (0.55 mole) of p-aminophenol, 43.28 g of a 50% by weight aqueous solution of sodium hydroxide (0.54 mole NaOH), 112 cc dimethylsulfoxide and 120 cc toluene. The resultant mixture is heated to the boiling point for six hours under a nitrogen atmosphere to remove all of the water present by azeotropic distillation. The reaction mixture is then allowed to cool to about 75° C., at which time 117 g (0.56 mole) of 2-methylchloropropyl methyldimethoxysilane are added dropwise while the reaction mixture is stirred. Following completion of the addition the reaction mixture is heated at 115° C. for about 16 hours, following which the mixture is allowed to cool and is filtered to remove any solid material. The solvents are then removed under a pressure of about 15 mm of mercury at a temperature of about 60° C. The pressure is then reduced to 2 mm of mercury and the material boiling at 165° C. is collected. Analysis by vapor phase chromatography indicates that the purity of the product, a pale yellow viscous liquid, was greater than 98%.

Workup

  1. customto remove all of the water present
  2. distillationby azeotropic distillation
  3. additionare added dropwise while the reaction mixture
  4. additioncompletion of the addition the reaction mixture
  5. temperatureto cool
  6. filtrationis filtered
  7. customto remove any solid material
  8. customThe solvents are then removed under a pressure of about 15 mm of mercury at a temperature of about 60° C
  9. customthe material boiling at 165° C. is collected

Sources & evidence

ORD record
ord-61ad4f733e6d4c6888e1b2f8b523b3bc
Source dataset
uspto-grants-1987_02
Patent number
US04645844

Reaction notes

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