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

HRID 1531476
Notes
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Reaction equation

HRID 1531476 reaction equation
[C:1]([O-:5])(=O)[CH2:2][OH:3].C=C.[K+].[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 962WaterHCID 86756524Mono-potassium ethylene glycolate2×

Product 1

HCID 760702-(2,4-Dinitrophenoxy)ethanolYield 92%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent2×

Conditions

Temperature
65 °C

Procedure

200 ml of ethylene glycol and 40 ml of the mono-potassium ethylene glycolate solution prepared under Example 3 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-dinitro-chloro-benzene and the remainder of the mono-potassium 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 169.7 g of 2-(2′,4′-dinitrophenoxy)-ethanol in a purity of 92%. Hence, a yield of 92% is achieved based on 2,4-dinitrochlorobenzene.

Workup

  1. additionwere introduced initially under nitrogen
  2. customfitted with a stirrer
  3. customThe precipitate which formed
  4. filtrationwas filtered off
  5. washwashed with 1000 ml of water
  6. customdried

Sources & evidence

ORD record
ord-f398d6fb983c4ef7a14e7d638084023a
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06198007B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes