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

HRID 2232769Notes

Reaction equation

HRID 2232769 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:9]/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=1.[N+:22]([C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)([O-:24])=[O:23].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([O:13][C:12](=[O:14])/[CH:11]=[CH:10]/[CH:9]=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347243(E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid

Product 1

HCID 14547245(E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid 4-nitrophenyl esterYield 109%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid (4.79 g) and 4-nitrophenol (2,5 g) in dichloromethane (50 mL) was treated with 1,3-dicyclohexylcarbodiimide (3.1 g). The mixture was stirred at 0°-5° C. for 1 hour, then at room temperature for 1 hour. The usual work up furnished 7.2 g of (E)-5,5-bis (3-chlorophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester as an essentially homogeneous by tlc. This material was used without further purification in subsequent reactions.

Workup

  1. waitat room temperature for 1 hour

Sources & evidence

ORD record
ord-83efb77cb6214cc5ac00a91b2a8d0ebb
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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