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Hydrochloric Acid → Phenol, 4-(2,2-dichloroethenyl)-

HRID 463905
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 463905
[ClH:1].C([N+](CC)(CC)CC)C.[C:11]1([CH3:21])[CH:16]=[CH:15]C(S(O)(=O)=O)=[CH:13][CH:12]=1.[Cl-:22].C([NH+](CC)CC)C.[CH2:30]([OH:32])[CH3:31]>O>[OH:32][C:30]1[CH:15]=[CH:16][C:11]([CH:12]=[C:13]([Cl:22])[Cl:1])=[CH:21][CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5413TetraethylammoniumHCID 6101p-Toluenesulfonic acidHCID 12698378Triethylazanium chloride

Produkt 1

HCID 5324901Phenol, 4-(2,2-dichloroethenyl)-Ausbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel

Versuchsvorschrift

A 10 ml quantity of concentrated hydrochloric acid, 2.5 g of tetraethyl ammonium salt of p-toluenesulfonic acid and 5.5 g of triethyl ammonium chloride were dissolved in 60 ml of ethanol. The solution was placed in an anode chamber and a cathode chamber separated from each other by a diaphragm. In the cathode chamber was further introduced 10 m mole of p-hydroxyphenyl trichloromethyl carbinol ##STR6## Then constant-current electrolysis was performed with use of lead as a cathode and carbon as an anode. After current (5 F/mole) was passed, the reaction liquid from the cathode chamber was added to 200 ml of water. The mixture was extracted four times with 50 ml of hexane. Then the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography, giving 1.80 g of p-hydroxy-β,β-dichlorostyrene ##STR7## Yield 95.2%, m.p. 90°-91° C. IR (cm-1) 3370, 1604, 1500, 1442, 1375, 1235, 1180, 1109, 909, 873, 821, 682.

Aufarbeitung

  1. customa cathode chamber separated from each other by a diaphragm
  2. customthe reaction liquid from the cathode chamber
  3. extractionThe mixture was extracted four times with 50 ml of hexane
  4. dry with materialThen the extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-940e57a83357473c904f523c36bf5794
Quelldatensatz
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04544766

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