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

HRID 1110517Notes

Reaction equation

HRID 1110517 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F: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]([F:21])[CH:16]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347239(E)-5,5-bis(3-fluorophenyl)-2,4-pentadienoic acid

Product 1

HCID 14347311(E)-5,5-bis(3-fluorophenyl)-2,4-pentadienoic acid 4-nitrophenyl esterYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E)-5,5-bis(3-fluorophenyl)-2,4-pentadienoic acid (20 g) and 4-nitrophenol (11.2 g) in dichloromethane (250 mL) was treated with 1,3-dicyclohexylcarbodiimide (14.7 g). The mixture was stirred at 0°-5° C. for 60 minutes, then at room temperature for 3 hours. After the usual work up, the ester was crystallized from dichloromethane-hexane to yield 26.1 g of (E)-5,5-bis (3-fluorophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester mp 129°-130° C. Recrystallization of a portion from the same solvents afforded the analytical sample, mp 129.5°-130.5° C. Anal. Calculated for C23H15F2NO4 : C, 67.81; H, 3.71; N, 3.44; F, 9.33 Found: C, 67.81; H, 3.74; N, 3.41; F, 9.37.

Workup

  1. waitat room temperature for 3 hours
  2. customAfter the usual work up, the ester was crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-757cdc1db34143b3b87c6a77570cff19
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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