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

HRID 511761Notes

Reaction equation

HRID 511761 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]>C(OCC)(=O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[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

5

Reactant 2

HCID 68962,6-DimethylanilineHCID 61525Hexafluoroacetone monohydrate

Product 1

HCID 12753462-(4-Amino-3,5-dimethylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-olYield 78%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.42 g of 2,6-dimethylaniline, 7.35 g of hexafluoroacetone hydrate, and 0.04 g of p-toluenesulfonic acid monohydrate was stirred under heating at 100° C. for 5 hours. After the temperature was returned to room temperature, the mixture was diluted with ethyl acetate and washed with a 1N sodium hydroxide aqueous solution. Then, the solvent was distilled off under reduced pressure, and the precipitated crude crystals were washed with a n-hexane-ethyl acetate mixed solvent to obtain 4.47 g (yield 78%) of the title compound as a solid.

Workup

  1. customwas returned to room temperature
  2. washwashed with a 1N sodium hydroxide aqueous solution
  3. distillationThen, the solvent was distilled off under reduced pressure
  4. customthe precipitated crude crystals
  5. washwere washed with a n-hexane-ethyl acetate mixed solvent

Sources & evidence

ORD record
ord-88136ac9a9a84a1c8f88f4d6228f5961
Source dataset
uspto-grants-2015_08
Patent number
US09101135B2

Reaction notes

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