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

HRID 13435

반응식

HRID 13435 반응식
[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

참가 물질

5

반응물 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

생성물 3

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

실험 절차

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%).

후처리

  1. customThe reaction liquid

출처 및 근거

ORD 기록
ord-b355d3dcfb4c4195b275a07f84f0f09b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728103B2

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