4-Nitrophenol → HCID 14347316, compound

HRID 2232768Notes

Reaction equation

HRID 2232768 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)=[CH:12]/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+:28]([C:31]1[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=1)([O-:30])=[O:29].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:28]([C:31]1[CH:36]=[CH:35][C:34]([O:16][C:15](=[O:17])/[CH:14]=[CH:13]/[CH:12]=[C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)=[CH:33][CH:32]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347254HCID 14347254, compound

Product 1

HCID 14347316HCID 14347316, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0.5 °C

Procedure

As in Example 115, (E)-5,5-bis (3,4-dimethoxyphenyl)-2,4-pentadienoic acid (16 g) and 4-nitrophenol (6.6 g) in dichloromethane (160 mL) was treated with 1,3-dicyclohexylcarbodiimide (9.3 g). The mixture was stirred at 0.5° C. for 1 hour, then at room temperature for 18 hours. After the usual work up, the crude product was triturated with ether to give 13.2 g of (E)-5,5-bis (3,4-dimethoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester. Crystallization of a portion from ether afforded the analytical sample, mp 140°-142° C.

Workup

  1. waitat room temperature for 18 hours
  2. customAfter the usual work up, the crude product was triturated with ether

Sources & evidence

ORD record
ord-217475560d5e4a76ae0fe499b415cb6f
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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