4-Nitrophenol → HCID 11047525, compound

HRID 2232863Notes

Reaction equation

HRID 2232863 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.[N+:21]([C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1)([O-:23])=[O:22].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([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)\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:26][CH:25]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 11108559HCID 11108559, compound

Product 1

HCID 11047525HCID 11047525, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid (4.5 g) and 4-nitrophenol (2.75 g) in 35 mL of dichloromethane was treated with 1,3-dicyclohexylcarbodiimide (3.4 g) and the mixture was stirred at room temperature for 4 hours. After the normal work up, crystallization of the crude ester from 2-propanol yielded 4.9 g of (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid 4-nitrophenyl ester, mp 75°-76° C.

Workup

  1. customAfter the normal work up, crystallization of the crude ester from 2-propanol

Sources & evidence

ORD record
ord-f2c6e3eb01d44accae6eccfe82eaffcd
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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