4-Nitrophenol → (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid 4-nitrophenyl ester

HRID 1651252Notes

Reaction equation

HRID 1651252 reaction equation
[CH2:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH3:16])=[CH:7][C:6]=1/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[CH2:2][CH2:3][CH3:4].[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:20][C:19](=[O:21])/[CH:18]=[CH:17]/[C:6]2[CH:7]=[C:8]([O:15][CH3:16])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]=2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14742799(E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid

Product 1

HCID 14742811(E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid 4-nitrophenyl esterYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 113, (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid (3.7 g) was reacted with 4-nitrophenol (1.99 g) in dichloromethane (40 mL) in the presence of 1,3-dicyclohexylcarbodiimide (2.7 g). The crude reaction product was crystallized from 2-propanol to give 4.63 g of (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid 4-nitrophenyl ester, mp 121.5°-122.5° C. Anal. Calcd for C24H23NO5 : C, 71.10; H, 5.72; N, 3.45 Found: C, 70.93; H, 5.77; N, 3.52

Workup

  1. customThe crude reaction product
  2. customwas crystallized from 2-propanol

Sources & evidence

ORD record
ord-22e2c0a1bd444435b8d0d2f5b8d2b5ca
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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