4-Nitrophenol → HCID 14347318, compound

HRID 1110528Notes

Reaction equation

HRID 1110528 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:9](/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10]\[CH:11]=[CH:12]\[C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=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: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:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347298HCID 14347298, compound

Product 1

HCID 14347318HCID 14347318, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (2E,4Z)-5-(3-methoxyphenyl)-5-phenyl-2,4-pentadienoic acid (2.85 g) and 4-nitrophenol (1.56 g) in dichloromethane (35 mL) was treated with 1,3-dicyclohexylcarbodiimide (2.1 g) and the mixture was stirred at room temperature for 75 minutes. The usual work up furnished 3.5 g of crude product which was crystallized from 2-propanol to give 3.0 g of (2E,4Z)-5-(3-methoxyphenyl)-5-phenyl-2,4-pentadienoic acid 4-nitrophenyl ester mp 155°-157° C. Anal. Calculated for C24H19NO5 : C, 71.81; H, 4.77; N, 3.49 Found: C, 72.09; H, 5.03; N, 3.55.

Workup

  1. customThe usual work up furnished 3.5 g of crude product which
  2. customwas crystallized from 2-propanol

Sources & evidence

ORD record
ord-f5acc910712b493ea1c6e4bd24feba7c
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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