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

HRID 703401Notes

Reaction equation

HRID 703401 reaction equation
[C:1]1([N:7]([C:47]2[CH:48]=[C:49]([CH3:53])[CH:50]=[CH:51][CH:52]=2)[C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][C:14]([N:21]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:22]5[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=5)=[CH:15][CH:16]=4)[C:11]([CH2:41][CH2:42][C:43](OC)=[O:44])([CH2:35][CH2:36][C:37](OC)=[O:38])[C:10]=3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[C:1]1([N:7]([C:47]2[CH:48]=[C:49]([CH3:53])[CH:50]=[CH:51][CH:52]=2)[C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][C:14]([N:21]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:22]5[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=5)=[CH:15][CH:16]=4)[C:11]([CH2:35][CH2:36][CH2:37][OH:38])([CH2:41][CH2:42][CH2:43][OH:44])[C:10]=3[CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

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 2,7-bis(phenyl-m-tolylamino)-9,9-bis[2-(methoxycarbonyl)ethyl]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 hours. Ten (10) percent aqueous sodium hydroxide solution was slowly added to the reaction mixture. The organic layer was separated and evaporated to dryness under reduced pressure. The residue was 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 pure 2,7-bis(phenyl-m-tolylamino)-9,9-bis(3-hydroxypropyl)fluorene, melting point 216° to 217° C.

Workup

  1. customThe organic layer was separated
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue was 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-e9af882bb02d41809909d480ac405f5c
Source dataset
uspto-grants-1991_01
Patent number
US04983482

Reaction notes

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