4-Nitrophenol → HCID 15097574, compound

HRID 1651226Notes

Reaction equation

HRID 1651226 reaction equation
[CH2:1]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][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[CH2:7][CH2:8][C:9]3[C:14](=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[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 14742801HCID 14742801, compound

Product 1

HCID 15097574HCID 15097574, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 113, (E)-3-(1-butyl-3,4-dihydro-6-methoxy-2-naphthalenyl)-2-propenoic acid (1.8 g) was reacted with 4-nitrophenol (0.97 g) in dichloromethane (30 mL) in the presence of 1,3-dicyclohexylcarbodiimide (1.3 g) overnight at room temperature. The normal work up yielded 1.5 g of crude ester. Crystallization from diethyl ether-2-propanol furnished (E)-3-(1-butyl-3,4-dihydro-6-methoxy-2-naphthalenyl)-2-propenoic acid 4-nitrophenyl ester, mp 94°-95° C. Anal. Calcd for C24H25NO5 : C, 70.74; H, 6.18; N, 3.44 Found: C, 70.42; H, 6.04; N, 3.29

Workup

  1. customCrystallization from diethyl ether-2-propanol

Sources & evidence

ORD record
ord-996d63a8d989441bac58663cb2aeefd6
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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