4-Nitrophenol → HCID 11047525, compound

HRID 2232870Notes

Reaction equation

HRID 2232870 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][CH2:20]CCCCCCC)=[CH:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.[N+:28]([C:31]1[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=1)([O-:30])=[O:29].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:28]([C:31]1[CH:36]=[CH:35][C:34]([O:15][C:13](=[O:14])/[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:33][CH:32]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347297HCID 14347297, compound

Product 1

HCID 11047525HCID 11047525, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (E,E)-5-(4-methoxyphenyl)-2,4-heptadecadienoic acid (7.5 g) and 4-nitrophenol (3.77 g) in 30 mL of dichloromethane was treated with 1,3-dicyclohexylcarbodiimide (4.2 g). The mixture was stirred at room temperature for 3 days to give, after the usual work up, 8.5 crude ester. The material was purified by HPLC (ether-hexane; 1:7), then was crystallized from 2-propanol to furnish 5.88 g of (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid 4-nitrophenyl ester, mp 46°-47° C.

Workup

  1. customto give
  2. customThe material was purified by HPLC (ether-hexane; 1:7)
  3. customwas crystallized from 2-propanol

Sources & evidence

ORD record
ord-31faf58cbc5649d0b538cb5a2b3ccf48
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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