4-Nitrophenol → HCID 14347444, compound

HRID 1110612Notes

Reaction equation

HRID 1110612 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:9](/[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=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:14][C:13](=[O:15])/[CH:12]=[CH:11]/[CH:10]=[C:9](/[C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)\[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 14347302HCID 14347302, compound

Product 1

HCID 14347444HCID 14347444, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E,E)-5-(3-methoxyphenyl)-2,4-nonadienoic acid (4.48 g) and 4-nitrophenol (2.97 g) in 25 mL of dichloromethane was treated with 1,3-dicyclohexylcarbodiimide (3 59 g). The mixture was stirred at room temperature for 3 days and after the normal work up. the crude product was crystallized from 2-propanol yield 5.6 g of (E,E)-5-(3-methoxyphenyl)-2,4-nonadienoic acid 4-nitrophenyl ester, mp 81.5°-83° C. Anal. Calcd for C22H23NO5 : C, 69.29; H, 6.08; N, 3.67. Found: C, 68.89; H, 6.08; N, 3.64.

Workup

  1. customthe crude product was crystallized from 2-propanol yield 5.6 g of (E,E)-5-(3-methoxyphenyl)-2,4-nonadienoic acid 4-nitrophenyl ester, mp 81.5°-83° C

Sources & evidence

ORD record
ord-3c9bf813f99a4f6ea43757341b0f0eb5
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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