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

HRID 501854Notes

Reaction equation

HRID 501854 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-nitrophenoxy]-acetic acid-2-hydroxyethyl ester 23 (100 grams, 410 mmol) and 2-(4-nitrophenoxy)-propionic acid 29 (95 g, 450 mmol ) in anhydrous dichloromethane (1000 ml) under nitrogen atmosphere was added dropwise a solution of 1,3-dicyclohexyl carbodiimide (240 g, 1160 mmol) in anhydrous dichloromethane (600 ml). The reaction mixture was stirred at room temperature for 12 hrs. The solids were filtered off and dichloromethane distilled off to get crude 38. The crude 38 was purified by column chromatography on silica gel using benzene as eluant to give pure 38 (53 grams, 29%) as a yellow low melting solid.

Workup

  1. filtrationThe solids were filtered off
  2. distillationdichloromethane distilled off
  3. customto get crude 38
  4. customThe crude 38 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-807cdd687df049828782657142df3921
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Reaction notes

Loading…