4-Nitrophenol → HCID 14347441, compound

HRID 2232867Notes

Reaction equation

HRID 2232867 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[C:8](/[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:9]\[CH:10]=[CH:11]\[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=1.[N+:20]([C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1)([O-:22])=[O:21].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([O:13][C:12](=[O:14])/[CH:11]=[CH:10]/[CH:9]=[C:8](\[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)/[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:25][CH:24]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347305HCID 14347305, compound

Product 1

HCID 14347441HCID 14347441, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (2E,4Z)-5-(3-fluorophenyl)-2,4-decadienoic acid (3.3 g) and 4-nitrophenol (2.1 g) in 20 mL of dichloromethane was treated with 1,3-dicyclohexylcarbodiimide (2.67 g) and the mixture was stirred at room temperature for 3 days. After the usual work up, crystallization of the crude material from hexane gave 3.1 g of (2E,4Z)-5-(3-fluorophenyl)-2,4-decadienoic acid 4-nitrophenyl ester, mp 50°-51° C.

Workup

  1. customAfter the usual work up, crystallization of the crude material from hexane

Sources & evidence

ORD record
ord-f40852b0d084434aa0017934e36429de
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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