4-Nitrophenol → (E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester

HRID 2232772Notes

Reaction equation

HRID 2232772 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[CH:11]/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[N+:26]([C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1)([O-:28])=[O:27].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:26]([C:29]1[CH:34]=[CH:33][C:32]([O:15][C:14](=[O:16])/[CH:13]=[CH:12]/[CH:11]=[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:31][CH:30]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347259(E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid

Product 1

HCID 14547247(E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid 4-nitrophenyl esterYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid (0.78 g) and 4-nitrophenol (0.35 g) in dichloromethane (10 mL) was treated with 1,3-dicyclohexylcarbodiimide (0.47 g). The mixture was stirred at 0°-5° C. for 1 hour, then at room temperature for 1 hour. The usual work up furnished 1.01 g of crude (E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester. This intermediate was used without further purification.

Workup

  1. waitat room temperature for 1 hour

Sources & evidence

ORD record
ord-68984cf95d5e450ba6761ce659fdc2b1
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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