4-Nitrophenol → HCID 14347450, compound

HRID 2232853Notes

Reaction equation

HRID 2232853 reaction equation
[CH:1]1(/[C:4](/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:5]/[CH:6]=[CH:7]/[C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1.[N+:19]([C:22]1[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=1)([O-:21])=[O:20].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([O:9][C:8](=[O:10])/[CH:7]=[CH:6]/[CH:5]=[C:4](/[CH:1]2[CH2:3][CH2:2]2)\[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:24][CH:23]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347281HCID 14347281, compound

Product 1

HCID 14347450HCID 14347450, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (2E,4Z)-5-cyclopropyl-5-(4-methoxyphenyl)-2,4-pentadienoic acid (1.95 g) and 4-nitrophenol (1.33 g) in 15mL of dichloromethane was reacted with 1,3-dicyclohexylcarbodiimide (1.66 g) and the mixture was stirred at room temperature for 18 hours. After the work up, the crude ester was crystallized from 2-propanol to furnish 1.9 g of (2E,4Z)-5-cyclopropyl-5-(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester, mp 115.5°-116.5° C.

Workup

  1. customAfter the work up, the crude ester was crystallized from 2-propanol

Sources & evidence

ORD record
ord-00fc599632df4dbcb9190f2ebf1801b5
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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