Sodium Hydroxide → 2,7-Bis(phenyl-m-tolylamino)-9,9-bis(3-hydroxypropyl)fluorene

HRID 1721838Notes

Reaction equation

HRID 1721838 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][C:7]1([CH2:48][CH2:49][C:50](OC)=[O:51])[C:19]2[CH:18]=[C:17]([N:20]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:21]3[CH:22]=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=3)[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][C:10]([N:34]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:35]1[CH:36]=[C:37]([CH3:41])[CH:38]=[CH:39][CH:40]=1)=[CH:11][CH:12]=2)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[OH:51][CH2:50][CH2:49][CH2:48][C:7]1([CH2:6][CH2:5][CH2:3][OH:2])[C:8]2[CH:9]=[C:10]([N:34]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:35]3[CH:36]=[C:37]([CH3:41])[CH:38]=[CH:39][CH:40]=3)[CH:11]=[CH:12][C:13]=2[C:14]2[C:19]1=[CH:18][C:17]([N:20]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:21]1[CH:22]=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=1)=[CH:16][CH:15]=2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 145978792,7-Bis(phenyl-m-tolylamino)-9,9-bis[2-(methoxycarbonyl)ethyl]fluoreneHCID 21226445Aluminium lithium hydride

Product 1

HCID 145978802,7-Bis(phenyl-m-tolylamino)-9,9-bis(3-hydroxypropyl)fluoreneYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a well-stirred solution of 8.8 grams of 9,9-bis[2-(methoxycarbonyl)ethyl]-2,7-bis(phenyl-m-tolylamino)fluorene in 150 milliliters of dried tetrahydrofuran under a nitrogen atmosphere was added in small portions, 0.52 gram, of lithium aluminum hydride over a period of 15 to 30 minutes. The reaction mixture was stirred at room temperature for two hous. Ten percent aqueous sodium hydroxide solution was then slowly added to the reaction mixture. The organic layer was separated and evaporated to dryness under reduced pressure. The residue as dissolved in methylene chloride, and washed several times with water. Evaporation of the dry methylene chloride solution provided a white solid, which was recrystallized from isopropanol and water to yield 7.8 grams of the above fluorene pure product, melting point, 216° to 217° C.

Workup

  1. customThe organic layer was separated
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue as dissolved in methylene chloride
  4. washwashed several times with water
  5. customEvaporation of the dry methylene chloride solution
  6. customprovided a white solid, which
  7. customwas recrystallized from isopropanol and water

Sources & evidence

ORD record
ord-133c1a59fe694d91b08e83dac7ea8595
Source dataset
uspto-grants-1989_08
Patent number
US04853308

Reaction notes

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