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

HRID 83802Notes

Reaction equation

HRID 83802 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].O[CH2:17][CH2:18][O:19][C:20](=[O:33])[CH:21]([O:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[CH3:22].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:13])[C:10]([O:12][CH2:17][CH2:18][O:19][C:20](=[O:33])[CH:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[CH3:22])=[O:11])=[CH:14][CH:15]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 38051392-(4-Nitrophenoxy)propanoic acidHCID 592539752-(4-Nitrophenoxy)-propionic acid 2-hydroxy-ethyl ester

Product 1

HCID 592539622-(4-Nitrophenoxy)propionic acid 2-[2-(4-nitrophenoxy)propionyloxy]ethyl esterYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-(4-nitrophenoxy)-propionic acid 29 (25 g, 118.5 mmol) and 2-(4-nitrophenoxy)propionic acid 2-hydroxyethyl ester 30 (25 g, 108 mmol) in anhydrous dichloromethane (625 ml) under nitrogen atmosphere was added dropwise a solution of 1,3-dicyclohexyl carbodiimide (40 g, 194 mmol) in anhydrous dichloromethane (250 ml). The reaction mixture was stirred at room temperature for 8 hours. The solids were filtered off and dichloromethane distilled off to get crude 31. The crude 31 was purified by column chromatography on silica gel using hexane as eluant to get pure 31 (17 g, 35.1%) as a white powder with an m.p. between 117.5-120.5° C.

Workup

  1. filtrationThe solids were filtered off
  2. distillationdichloromethane distilled off
  3. customto get crude 31
  4. customThe crude 31 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b22f2fb492be470e9611853c66aefd82
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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