Dicyclohexylcarbodiimide → 2-(4-Nitrophenoxy)-propionic acid 2-[2-(4-nitrophenoxy)-acetoxy]-ethyl ester

HRID 2169737Notes

Reaction equation

HRID 2169737 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5](=[O:17])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[N+:18]([C:21]1[CH:32]=[CH:31][C:24]([O:25][CH:26]([CH3:30])[C:27](O)=[O:28])=[CH:23][CH:22]=1)([O-:20])=[O:19].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]([O:4][CH2:3][CH2:2][O:1][C:27](=[O:28])[CH:26]([O:25][C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:32][CH:31]=2)[CH3:30])=[O:17])=[CH:9][CH:10]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 38051392-(4-Nitrophenoxy)propanoic acidHCID 59253945(4-Nitrophenoxy)-acetic acid-2-hydroxy-ethyl ester

Product 1

HCID 592539882-(4-Nitrophenoxy)-propionic acid 2-[2-(4-nitrophenoxy)-acetoxy]-ethyl esterYield 29.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-nitrophenoxyacetic acid-2-hydroxyethyl ester 41 (100 g, 410 mmol) and 2-(4-nitrophenoxy)propionic acid 47 (95 g, 450 mmol) in anhydrous dichloromethane (1000 ml) under nitrogen atm. was added a solution of 1,3-dicyclohexylcarbodiimide (240 g, 1160 mmol) in anhydrous dichloromethane (600 ml) dropwise. The reaction mixture was stirred at room temperature for 12 hrs. The solids were filtered off and dichloromethane distilled off to get crude 55. The crude 55 was purified by column chromatography on silica gel using benzene as eluant to give pure 55 (53 g, 29%) as a yellow low melting solid.

Workup

  1. filtrationThe solids were filtered off
  2. distillationdichloromethane distilled off
  3. customto get crude 55
  4. customThe crude 55 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-106b48d7dcc946e188f0ea773bcd4f55
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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