Hydrochloric Acid → 3,3'-((9,9-dioctyl-9H-fluorene-2,7-diyl)bis(m-tolylazanediyl))dibenzaldehyde

HRID 42382Notes

Reaction equation

HRID 42382 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([N:12]([C:61]2[CH:62]=[C:63]([CH3:67])[CH:64]=[CH:65][CH:66]=2)[C:13]2[CH:25]=[CH:24][C:23]3[C:22]4[C:17](=[CH:18][C:19]([N:26]([C:34]5[CH:39]=[CH:38][CH:37]=[C:36]([CH:40]6OCC[O:41]6)[CH:35]=5)[C:27]5[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=5)=[CH:20][CH:21]=4)[C:16]([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C:15]=3[CH:14]=2)[CH:9]=[CH:10][CH:11]=1.Cl>CC(C)=O>[CH2:53]([C:16]1([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C:17]2[CH:18]=[C:19]([N:26]([C:34]3[CH:35]=[C:36]([CH:37]=[CH:38][CH:39]=3)[CH:40]=[O:41])[C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)[CH:20]=[CH:21][C:22]=2[C:23]2[C:15]1=[CH:14][C:13]([N:12]([C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH:2]=[O:1])[C:61]1[CH:62]=[C:63]([CH3:67])[CH:64]=[CH:65][CH:66]=1)=[CH:25][CH:24]=2)[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58028461HCID 58028461, compound

Product 1

HCID 580284603,3'-((9,9-dioctyl-9H-fluorene-2,7-diyl)bis(m-tolylazanediyl))dibenzaldehydeYield 90.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a three-neck round-bottom flask, were added 34.0 g N2,N7-bis(3-(1,3-dioxolan-2-yl)phenyl)-9,9-dioctyl-N2,N7-di-m-tolyl-9H-fluorene-2,7-diamine and in 1000 mL acetone. 189.5 mL 2 M hydrochloric acid solution was added slowly to the reaction mixture through an addition funnel. The reaction was monitored by TLC. After the reaction was done showed by TLC, the solvent was removed by evaporation. 1000 mL Ethyl acetate was added, and the reaction mixture was extracted using DI water (3×750 mL). The combined organic layer was dried over magnesium sulfate. After filtration, the solvent was removed by evaporation. The product (27.8 g) was obtained, and was carried on to next reaction without further purification. The structure was confirmed by NMR.

Workup

  1. customthe solvent was removed by evaporation
  2. addition1000 mL Ethyl acetate was added
  3. extractionthe reaction mixture was extracted
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-cc59a0d0fd4b424daff87e80c3c72591
Source dataset
uspto-grants-2013_09
Patent number
US08535974B2

Reaction notes

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