4-Nitrophenol → HCID 14347455, compound

HRID 1110608Notes

Reaction equation

HRID 1110608 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[CH:16]([CH3:18])[CH3:17])=[CH:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])=[CH:5][CH:4]=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:14][C:13](=[O:15])/[CH:12]=[CH:11]/[CH:10]=[C:9](/[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)\[CH:16]([CH3:18])[CH3:17])=[CH:24][CH:23]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347289HCID 14347289, compound

Product 1

HCID 14347455HCID 14347455, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E,E)-5-(4-methoxyphenyl)-6-methyl-2,4-heptadienoic acid (2,4 g) and 4-nitrophenol (1.63 g) in 15 mL of dichloromethane was treated with 1,3-dicyclohexylcarbodiimide (2.02 g) and the mixture was stirred at room temperature for 18 hours. Crystallization of the crude product from 2-propanol-hexane yielded 2.85 g of (E,E)-5-(4-methoxyphenyl)-6-methyl-2,4-heptadienoic acid 4-nitrophenyl ester, mp 95°-96.5° C.

Workup

  1. customCrystallization of the crude product from 2-propanol-hexane

Sources & evidence

ORD record
ord-168a6947960243949a40f25229c0ea2a
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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