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

HRID 429403Notes

Reaction equation

HRID 429403 reaction equation
O.O.O.[F:4][C:5]([F:13])([F:12])[C:6]([C:8]([F:11])([F:10])[F:9])=[O:7].[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH2:17]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:4][C:5]([F:13])([F:12])[C:6]([C:20]1[CH:19]=[C:18]([CH3:22])[C:16]([NH2:17])=[C:15]([CH3:14])[CH:21]=1)([OH:7])[C:8]([F:11])([F:10])[F:9]

Participants

4

Reactant 2

HCID 68962,6-DimethylanilineHCID 36719Hexafluoroacetone trihydrate

Product 1

HCID 12753462-(4-Amino-3,5-dimethylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-olYield 87%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Conditions

Temperature
130 °C

Procedure

Hexafluoroacetone trihydrate (9.68 g, 44 mmol) was added to 2,6-dimethylaniline (4.84 g, 40 mmol) and p-toluenesulfonic acid (304 mg, 1.6 mmol) at room temperature. The mixture was stirred at 130° C. for 14 hours under a nitrogen atmosphere. After cooling down, the solidified mixture was washed with sodium bicarbonate solution, water, and hexane and dried to afford 10 g of 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2,6-dimethylaniline. 1H NMR (DMSO): δ 8.11 (s, 1H), 7.08 (s, 2H), 4.89 (s, 2H), 2.10 (s, 6H). MS (ES) m/z 288.1 ([M+H]+).

Workup

  1. temperatureAfter cooling down
  2. washthe solidified mixture was washed with sodium bicarbonate solution, water, and hexane
  3. customdried

Sources & evidence

ORD record
ord-1a75afd70821400a873211559678c2b4
Source dataset
uspto-grants-2001_11
Patent number
US06316503B1

Reaction notes

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