4-Nitrophenol → HCID 14742808, compound

HRID 1651238Notes

Reaction equation

HRID 1651238 reaction equation
[CH2:1]([C:5]1[C:14]2[C:9](=[C:10]([O:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[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]=[CH:8][C:9]3[C:14](=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])[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 14742796HCID 14742796, compound

Product 1

HCID 14742808HCID 14742808, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 113, (E)-3-(1-butyl-5-methoxy-2-naphthalenyl)-2-propenoic acid (1.4 g) was reacted with 4-nitrophenol (0.76 g) in dichloromethane (25 mL) in the presence of 1,3-dicyclohexylcarbodiimide (1.02 g) to give 1.51 g of (E)-3-(1-butyl-5-methoxy-2-naphthalenyl)-2-propenoic acid 4-nitrophenyl ester. Crystallization of a portion from diethyl ether afforded the analytical sample, mp 115°-116° C. Anal. Calcd for C24H23NO5 : C, 71.10; H, 5.72; N, 3.45 Found: C, 71.25; H, 5.75; N, 3.39

Sources & evidence

ORD record
ord-7650530729bd4e4eb3fe52c5c7f9dc7b
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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