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4-Nitrophenol → 2-Propanol, 1,3-bis(p-nitrophenoxy)-

HRID 2120321
Notes
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Reaction equation

HRID 2120321 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1>C1(C)C(C)=CC=CC=1>[N+:7]([C:6]1[CH:5]=[CH:4][C:3]([O:10][CH2:2][CH:3]([OH:10])[CH2:4][O:10][C:3]2[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=2)=[CH:2][CH:1]=1)([O-:9])=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 9804-Nitrophenol

Product 1

HCID 4590272-Propanol, 1,3-bis(p-nitrophenoxy)-

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

76.5 g (0.55 mole) of p-nitrophenol, 32.3 g (0.25 mole) of glycerol-αα′-dichlorohydrin, and 500 ml of xylene were added to a reaction solution, and the reaction mixtures were heated with stirring under a nitrogen current. After dissolving the solid, 345 g (2.5 moles) of potassium carbonate anhydride was added, and the reaction mixtures were refluxed with stirring for 12 hours. The reacted solution was separated by filtration while it was warm. After cooling, hexane was added to the filtrate. A yellow viscous liquid was obtained. After column purification and drying this liquid, a 55 g-yellow viscous liquid (1,3-bis (4-nitrophenoxy)-2-propyl alcohol) was obtained.

Workup

custom
the reaction mixtures
  • temperaturewere heated
  • additionwas added
  • customthe reaction mixtures
  • temperaturewere refluxed
  • stirringwith stirring for 12 hours
  • customThe reacted solution was separated by filtration while it
  • temperaturewas warm
  • temperatureAfter cooling
  • additionhexane was added to the filtrate
  • customA yellow viscous liquid was obtained
  • customAfter column purification
  • customdrying this liquid
  • Sources & evidence

    ORD record
    ord-3a093f462d024b53bfa3715945a97110
    Source dataset
    uspto-grants-2004_02
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US06689899B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes