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3,3'-Bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4'-oxydianiline → 4,4'-Diaminodiphenyl Ether

HRID 13435
Notes
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Reaction equation

HRID 13435 reaction equation
[OH:1][C:2]([C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][C:20]=1[C:26]([C:32]([F:35])([F:34])[F:33])([OH:31])[C:27]([F:30])([F:29])[F:28])[NH2:14])([C:7]([F:10])([F:9])[F:8])[C:3]([F:6])([F:5])[F:4].OC([C:46]1[CH:47]=[C:48]([CH:50]=[CH:51][C:52]=1[O:53][C:54]1[CH:60]=[CH:59][C:57]([NH2:58])=[CH:56][CH:55]=1)[NH2:49])(C(F)(F)F)C(F)(F)F>>[F:4][C:3]([F:6])([F:5])[C:2]([C:7]([F:10])([F:9])[F:8])=[O:1].[OH:31][C:26]([C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:19]=1[O:18][C:17]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][C:11]=1[C:2]([C:3]([F:4])([F:5])[F:6])([OH:1])[C:7]([F:8])([F:9])[F:10])[NH2:23])([C:27]([F:30])([F:29])[F:28])[C:32]([F:35])([F:34])[F:33].[O:53]([C:54]1[CH:60]=[CH:59][C:57]([NH2:58])=[CH:56][CH:55]=1)[C:52]1[CH:46]=[CH:47][C:48]([NH2:49])=[CH:50][CH:51]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 866233913,3'-Bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4'-oxydianilineHCID 866233923-(1-Hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4'-oxydianiline

Product 3

HCID 75794,4'-Diaminodiphenyl EtherHCID 12695HexafluoroacetoneHCID 866233913,3'-Bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4'-oxydianiline

Procedure

The reaction liquid was found by gas chromatography (GC) analysis to contain 60.1% of the target compound, 3,3′-bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4′-oxydianiline, 25.0% of 3-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4′-oxydianiline, and 14.4% of the total of various imines produced by the reaction of hexafluoroacetone with the amine moiety of 4,4′-oxydianiline. 100 ml of water were added to the reaction liquid, followed by extraction with 100 ml of ethyl acetate. Then, the organic layer was washed with 50 ml of saturated sodium hydrogencarbonate aqueous solution. The organic layer was dried with magnesium sulfate, followed by filtration and distilling the solvent off, thereby obtaining 112 g of crude 3,3′-bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4′-oxydianiline (purity: 50.7%). This crude product was recrystallized in toluene, thereby obtaining 41.0 g of the target 3,3′-bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4′-oxydianiline (yield: 62%; purity: 95.7%).

Workup

  1. customThe reaction liquid

Sources & evidence

ORD record
ord-b355d3dcfb4c4195b275a07f84f0f09b
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728103B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes