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Ethylene carbonate → 4-(2-Hydroxyethoxy)-p-quaterphenyl

HRID 1085879
Notes
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Reaction equation

HRID 1085879 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1(=O)O[CH2:29][CH2:28][O:27]1>>[OH:27][CH2:28][CH2:29][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 7303Ethylene carbonateHCID 235086234-Hydroxy-p-quaterphenyl

Product 1

HCID 541393194-(2-Hydroxyethoxy)-p-quaterphenylYield 83%

Procedure

First, 19.2 g (60 mmol) of the HQ obtained in section (M) mentioned above was put in an 1-liter three-necked flask, and dissolved by the addition of 500 ml of sulforane. To this solution, 7.92 g (90 mmol) of ethylene carbonate was added, and the mixture was heated under a nitrogen atmosphere. Then 0.1 g of K2C03 was added at the reflux temperature of sulforane, and reflux was continued for 4 hours with stirring. After the reaction was completed, the reaction mixture was filtered and the filtrate was cooled. The white solid that was precipitated was collected by filtration and dried. In this way, 18.38 g (yield, 83% of 4-(2-hydroxyethoxy)-p-quaterphenyl (HEQ) was obtained. The liquid-crystal transition temperature of HEQ was 335° C.

Workup

  • customabove was put in an 1-liter three-necked flask
  • dissolutiondissolved by the addition of 500 ml of sulforane
  • temperaturethe mixture was heated under a nitrogen atmosphere
  • additionThen 0.1 g of K2C03 was added at the reflux temperature of sulforane
  • temperaturereflux
  • filtrationthe reaction mixture was filtered
  • temperaturethe filtrate was cooled
  • customThe white solid that was precipitated
  • filtrationwas collected by filtration
  • customdried
  • customIn this way, 18.38 g (yield
  • Sources & evidence

    ORD record
    ord-a11983b204e04319a8208c3deecc86c9
    Source dataset
    uspto-grants-1991_04
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US05011879

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes