Potassium Carbonate → bis[6-{4-[(1E)-3-(4-pentyloxyphenoxy)-3-oxoprop-1-enyl]phenoxy}hexyl]2,2 bis(4-nitrobenzyl)malonate

HRID 2246021Notes

Reaction equation

HRID 2246021 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9](=[O:41])[C:10]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Cl)=[O:12].[OH:42][C:43]1[CH:48]=[CH:47][C:46](/[CH:49]=[CH:50]/[C:51]([O:53][C:54]2[CH:59]=[CH:58][C:57]([O:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])=[CH:56][CH:55]=2)=[O:52])=[CH:45][CH:44]=1.[C:66](=[O:69])([O-])[O-:67].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(=O)CC>[CH2:61]([O:60][C:57]1[CH:56]=[CH:55][C:54]([O:53][C:51](=[O:52])/[CH:50]=[CH:49]/[C:46]2[CH:45]=[CH:44][C:43]([O:42][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9](=[O:41])[C:10]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=3)([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:42][C:43]3[CH:44]=[CH:45][C:46](/[CH:49]=[CH:50]/[C:66]([O:67][C:54]4[CH:55]=[CH:56][C:57]([O:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])=[CH:58][CH:59]=4)=[O:69])=[CH:47][CH:48]=3)=[O:12])=[CH:48][CH:47]=2)=[CH:59][CH:58]=1)[CH2:62][CH2:63][CH2:64][CH3:65]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 59217445Bis[6-chlorohexyl]2,2 bis(4-nitrobenzyl)malonateHCID 592174494-pentoxyphenyl (2E)-3-{4-hydroxyphenyl}acrylate

Product 1

HCID 59217452bis[6-{4-[(1E)-3-(4-pentyloxyphenoxy)-3-oxoprop-1-enyl]phenoxy}hexyl]2,2 bis(4-nitrobenzyl)malonateYield 65.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

2.80 g (4.6 mmol) bis[6-chlorohexyl]2,2 bis(4-nitrobenzyl)malonate, 3.0 g (9.2 mmol) 4-pentoxyphenyl (2E)-3-{4-hydroxyphenyl}acrylate and 0.17 g (0.46 mmol) tetrabutylammonium iodide were dissolved in 30 ml 2-butanone. 2.53 g (18.3 mmol) potassium carbonate were added. The resulting suspension was heated at refluxing temperature and allowed to react for 48 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation to yield 3.6 g bis[6-{4-[(1E)-3-(4-pentyloxyphenoxy)-3-oxoprop-1-enyl]phenoxy}hexyl]2,2 bis(4-nitrobenzyl)malonate.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat refluxing temperature
  3. customto react for 48 h
  4. customthe reaction mixture was partitioned between ethyl acetate and water
  5. washThe organic phase was washed repeatedly with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-ce48a12435f341ad8e83dfeb50492dd5
Source dataset
uspto-grants-2010_03
Patent number
US07687118B2

Reaction notes

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