P-Phenylenediamine → P-Phenylenediamine

HRID 2080352Notes

Reaction equation

HRID 2080352 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.O.O.[F:24][C:25]([F:33])([F:32])[C:26]([C:28]([F:31])([F:30])[F:29])=[O:27].[OH:34][C:35]([C:44]1[CH:49]=[C:48]([NH2:50])[CH:47]=[CH:46][C:45]=1[NH2:51])([C:40]([F:43])([F:42])[F:41])[C:36]([F:39])([F:38])[F:37]>>[F:24][C:25]([F:33])([F:32])[C:26]([C:28]([F:31])([F:30])[F:29])=[O:27].[OH:34][C:35]([C:44]1[CH:49]=[C:48]([NH2:50])[CH:47]=[CH:46][C:45]=1[NH2:51])([C:36]([F:39])([F:38])[F:37])[C:40]([F:43])([F:42])[F:41].[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 7814P-Phenylenediamine2×HCID 36719Hexafluoroacetone trihydrateHCID 521998p-Toluenesulfonic acid monohydrateHCID 595522702,5-Diamino-α,α-bis(trifluoromethyl)benzenemethanol

Product 3

HCID 7814P-PhenylenediamineHCID 12695HexafluoroacetoneHCID 595522702,5-Diamino-α,α-bis(trifluoromethyl)benzenemethanol

Procedure

A 100 ml, glass, sealed container (autoclave) was charged with 10.0 g (92.5 mmol) of 1,4-phenylenediamine, 704 mg (3.70 mmol, 4 mol %) of p-toluenesulfonic acid monohydrate, and 40.7 g (185 mmol, 2 equivalents) of hexafluoroacetone trihydrate, and the inside of the system was turned into a nitrogen atmosphere. Then, the temperature increased was started, and the inside temperature of the reaction liquid was set to 110° C. After stirring for 21 hours, the reaction liquid was cooled down. The reaction liquid was found by gas chromatography (GC) analysis to contain 75.5% of the target compound, 1-(2-hydroxyhexafluoro-2-propyl)-2,5-phenylenediamine, 3.6% of 1,4-phenylenediamine, and 20.9% of imines produced by the reaction of hexafluoroacetone with the amine moiety of 1,4-phenylenediamine. 200 ml of water were added to the reaction liquid, and it was cooled down in iced bath. The precipitated solid was filtered and vacuum dried, thereby obtaining 24.7 g (yield: 97%; purity: 78.9%) of crude 1-(2-hydroxyhexafluoro-2-propyl)-2,5-phenylenediamine. This crude product was recrystallized in toluene, thereby obtaining 18.6 g (yield: 73%; purity: 99.4%) of the target 1-(2-hydroxyhexafluoro-2-propyl)-2,5-phenylenediamine.

Workup

  1. customA 100 ml, glass, sealed container (autoclave)
  2. temperatureThen, the temperature increased
  3. customthe inside temperature of the reaction liquid
  4. customwas set to 110° C
  5. customthe reaction liquid
  6. temperaturewas cooled down
  7. customThe reaction liquid

Sources & evidence

ORD record
ord-375954c3c44e4663a8a6732e29bc7a34
Source dataset
uspto-grants-2011_04
Patent number
US07932348B2

Reaction notes

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