4-Nitrophenol → HCID 14347314, compound

HRID 1110519Notes

Reaction equation

HRID 1110519 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[CH:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=1.[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:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[CH:29][CH:28]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347241(E)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid

Product 1

HCID 14347314HCID 14347314, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid (49.6) and 4-nitrophenol (25 g) in dichloromethane (600 mL) was treated with 1,3-dicyclohexylcarbodiimide (33 g). The mixture was stirred at 0°-5° C. for 1 hour, then at room temperature for 2 hours. After the usual work up, the crude product (67 g) was crystallized from 2-propanol-ether-hexane to give 61.0 g of (E)-5,5-bis (3-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester mp 95°-97° C. Recrystallization of a portion from dichloromethane-hexane yielded the analytical sample, mp 99°-100° C. Anal. Calculated for C25H21NO6 : C, 69.60; H, 4.91; N, 3.23 Found: C, 69.62; H, 5.04; N, 3.23.

Workup

  1. waitat room temperature for 2 hours
  2. customAfter the usual work up, the crude product (67 g) was crystallized from 2-propanol-ether-hexane

Sources & evidence

ORD record
ord-76e98a0cf7574eb3baacdd7b0f783cfb
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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