4-Nitrophenol → HCID 14742807, compound

HRID 1651223Notes

Reaction equation

HRID 1651223 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)[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]=[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 14742795HCID 14742795, compound

Product 1

HCID 14742807HCID 14742807, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred mixture of (E)-3-(1-butyl-6-methoxy-2-naphthalenyl)-2-propenoic acid (1.5 g) and 4-nitrophenol (0.81 g) in dichloromethane, was cooled in an ice bath, during the addition of a solution of 1,3-dicyclohexyl- carbodiimide (1.1 g) in dichloromethane (5 mL) then the reaction was stirred at room temperature over the weekend. After the precipitated dicyclohexylurea was removed by filtration, the filtrate was concentrated and applied to a column of silica gel (25 g) made up in dichloromethane-hexane (2:1). Elution with the same solvent mixture and concentration of the appropriate fractions yielded 2 g of (E)-3-(1-butyl-6-methoxy-2-naphthalenyl)-2-propenoic acid 4-nitrophenyl ester. Crystallization of the material from 2-propanol gave 1.85 g of the active ester, mp 140°-141° C. Anal. Calcd for C24H23NO5 : C, 71.10; H, 5.72; N, 3.45 Found: C, 70.98; H, 5.50; N, 3.33

Workup

  1. customAfter the precipitated dicyclohexylurea was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. washElution with the same solvent mixture and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-4e4f5e3db11845839c22ca3c7803f45e
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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