4-Nitrophenol → HCID 14347442, compound

HRID 1110619Notes

Reaction equation

HRID 1110619 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[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:4][CH:3]=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:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=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 14347306HCID 14347306, compound

Product 1

HCID 14347442HCID 14347442, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E,E)-5-(4-fluorophenyl)-2,4-decadienoic acid (4.78 g) and 4-nitrophenol (3.14 g) in 20 mL of dichloromethane was treated with 1,3- dicyclohexylcarbodiimide (3.8 g) and the mixture was stirred at room temperature for 3 days. After the usual work up. crystallization of the crude ester from 2-propanol-hexane gave 4.86 g of (E,E)-5-(4-fluorophenyl)-2,4-decadienoic acid 4-nitrophenyl ester, mp 71°-72,5° C.

Workup

  1. customcrystallization of the crude ester from 2-propanol-hexane

Sources & evidence

ORD record
ord-0ede267a8bee4a79813dc6cf94176927
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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