4-Nitrophenol → HCID 14347439, compound

HRID 1110616Notes

Reaction equation

HRID 1110616 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](/[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12]/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+:23]([C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1)([O-:25])=[O:24].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:23]([C:26]1[CH:31]=[CH:30][C:29]([O:16][C:15](=[O:17])/[CH:14]=[CH:13]/[CH:12]=[C:11](/[C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:28][CH:27]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347307HCID 14347307, compound

Product 1

HCID 14347439HCID 14347439, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E,E)-5-(3,4-dimethoxyphenyl)-2,4-decadienoic acid (3.08 g) and 4-nitrophenol (2.7 g) in 20 mL of dichloromethane was treated with 1,3-dicyclohexylcarbodiimide (2.11 g). The mixture was stirred at room temperature for 3 days and after the usual word up crystallization of the crude ester from 2-propanol-hexane gave 2.98 g of (E,E)-5-(3,4-dimethoxyphenyl)-2,4-decadienoic acid 4-nitrophenyl ester, mp 95-°96.5° C.

Workup

  1. customafter the usual word up crystallization of the crude ester from 2-propanol-hexane

Sources & evidence

ORD record
ord-4064ff0e65f94761a024fd40e9a7724b
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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