2,6-Dimethylaniline → 2-(4-Amino-3,5-dimethylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

HRID 1696956Notes

Reaction equation

HRID 1696956 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].O.[F:11][C:12]([F:20])([F:19])[C:13]([C:15]([F:18])([F:17])[F:16])=[O:14].[OH-].[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>[CH3:1][C:2]1[CH:8]=[C:7]([C:13]([OH:14])([C:15]([F:18])([F:17])[F:16])[C:12]([F:20])([F:19])[F:11])[CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4]

Participants

6

Reactant 3

HCID 68962,6-DimethylanilineHCID 14798Sodium HydroxideHCID 61525Hexafluoroacetone monohydrate

Product 1

HCID 12753462-(4-Amino-3,5-dimethylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-olYield 69%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

While 24.4 g of 2,6-dimethylaniline and 50.0 g of hexafluoroacetone hydrate were mixed at room temperature, 0.5 g of p-toluenesulfonic acid monohydrate was added thereto. The reaction solution was stirred at 100 degree centigrade. After disappearance of the starting raw material was confirmed by means of TLC, to the reaction solution were added ethyl acetate and 1N aqueous sodium hydroxide solution for solution separation and extraction. Anhydrous magnesium sulfate was added to an organic layer, and the organic layer was dried and then filtered off. The filtrate was concentrated under a reduced pressure, and then hexane was added to the residue for washing. The suspension was filtered and the resulting filtered product was vacuum-dried at room temperature to obtain 24.3 g of the desired product (Yield: 69%) in the form of powder.

Workup

  1. customfor solution separation and extraction
  2. additionAnhydrous magnesium sulfate was added to an organic layer
  3. customthe organic layer was dried
  4. filtrationfiltered off
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. additionhexane was added to the residue
  7. washfor washing
  8. filtrationThe suspension was filtered
  9. filtrationthe resulting filtered product
  10. customwas vacuum-dried at room temperature

Sources & evidence

ORD record
ord-972703c77e2041579c42ca7242345efe
Source dataset
uspto-grants-2012_04
Patent number
US08163804B2

Reaction notes

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