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

HRID 1110518Notes

Reaction equation

HRID 1110518 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:9]/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=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:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347251(E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid

Product 1

HCID 14347312(E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid 4-nitrophenyl esterYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid (23.75 g) and 4-nitrophenol (12.7 g) in dichloromethane (250 mL) was treated with 1,3-dicyclohexylcarbodiimide (17.12 g). The mixture was stirred at 0°-5° C. for 60 minutes and then at room temperature for 1 hour. After the usual work up, the crude product was crystallized from 2-propanol to give 26.5 g of (E)-5,5-bis (4-fluorophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester mp 112°-114° C. Recrystallization of a portion from the same solvent yielded the analytical sample, mp 112.5°-114° C. Anal. Calculated for C23H15F2NO4 :C, 67.81; H, 3.71; N, 3.44; F, 9.33 Found: C, 67.76; H, 3.77; N, 3.48; F, 9.11.

Workup

  1. waitat room temperature for 1 hour
  2. customAfter the usual work up, the crude product was crystallized from 2-propanol

Sources & evidence

ORD record
ord-3bfd0ce4a56b415c9715c62d201ae46f
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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