4-Nitrophenol → HCID 14347438, compound

HRID 2232851Notes

Reaction equation

HRID 2232851 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])=[CH:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14].[N+:24]([C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1)([O-:26])=[O:25].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:24]([C:27]1[CH:32]=[CH:31][C:30]([O:14][C:13](=[O:15])/[CH:12]=[CH:11]/[CH:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])=[CH:29][CH:28]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347263HCID 14347263, compound

Product 1

HCID 14347438HCID 14347438, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E)-5,5-bis(2-methoxyphenyl)-2,4-pentadienoic acid (5 g) and 4-nitrophenol (2.7 g) in dichloromethane (35 mL) was treated with 1,3-dicyclohexylcarbodiimide (3.34 g). The mixture was stirred at 0°-5° C. for 30 minutes and then at room temperature for 18 hours. After the usual work up, the crude product was crystallized from 2-propanol to give 6.1 g of (E)-5,5-bis(2-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester, mp 141.5°-143° C. A portion from the 2-propanol to yield the analytical sample, mp 142°-143° C.

Workup

  1. waitat room temperature for 18 hours
  2. customAfter the usual work up, the crude product was crystallized from 2-propanol

Sources & evidence

ORD record
ord-9b511c7091fa49ebb0dd0a7dd31b952c
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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