1-Chloro-2,4-Dinitrobenzene → 2-(2,4-Dinitrophenoxy)ethanol

HRID 1531477

Reaction equation

HRID 1531477 reaction equation
[C:1]([O-:5])(=O)[CH2:2][OH:3].C=C.[Na+].[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1Cl)([O-:11])=[O:10].O>C(O)CO>[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[O:3][CH2:2][CH2:1][OH:5])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 962WaterHCID 23717809Mono sodium ethylene glycolate2×

Product 1

HCID 760702-(2,4-Dinitrophenoxy)ethanolYield 92.2%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent2×

Conditions

Temperature
65 °C

Procedure

200 ml of ethylene glycol and 40 ml of a 14.4% strength mono-sodium ethylene glycolate solution were introduced initially under nitrogen and were heated to 65° C. in a 2 l reaction vessel fitted with a stirrer. Over the course of 5 h, 162 g of molten 2,4-dinitrochlorbenzene and a further 480 ml of a 14.4% strength mono-sodium ethylene glycolate solution in ethylene glycol were simultaneously metered in. The mixture was then stirred for one hour at 65° C., and then 600 ml of water were added. The precipitate which formed was filtered off and washed with 1000 ml of water and dried, giving 161.3 g of 2-(2′,4′-dinitrophenoxy)-ethanol in a purity of 97%. Hence, a yield of 92.2% is achieved based on 2,4-dinitrochloro-benzene.

Workup

  1. customfitted with a stirrer
  2. customThe precipitate which formed
  3. filtrationwas filtered off
  4. washwashed with 1000 ml of water
  5. customdried

Sources & evidence

ORD record
ord-d1b19539d0164fdd89d11238c9ff9c7c
Source dataset
uspto-grants-2001_03
Patent number
US06198007B1

Linked notes

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