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Hydrochloric Acid → 4'-Phenylthio-2,4-dihydroxybenzophenone

HRID 1369327
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1369327
[OH:1][C:2]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9](Cl)=[CH:8][CH:7]=1)=[O:5].[C:18]1([SH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN1CCCC1=O>[C:18]1([S:24][C:9]2[CH:10]=[CH:11][C:6]([C:4](=[O:5])[C:3]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:2]=3[OH:1])=[CH:7][CH:8]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 519532(4-Chlorophenyl)(2,4-dihydroxyphenyl)methanone

Produkt 1

HCID 120842914'-Phenylthio-2,4-dihydroxybenzophenoneAusbeute 42,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387
N-methyl-2-pyrrolidone
Lösungsmittel

Versuchsvorschrift

A mixture of 39 g (156 mmol) of 2,4-dihydroxy-4′-chlorobenzophenone, 22.4 g (204 mmol) of thiophenol and 26 g (188 mmol) of potassium carbonate is stirred in 300 ml of N-methyl-2-pyrrolidone for 24 hours at a temperature of 210° C. After cooling the reaction mixture is neutralized with hydrochloric acid (10%) and extracted with 4×250 ml of ethyl acetate. The solution so obtained is washed with water and afterwards with a saturated solution of sodium chloride. The residue which is obtained, after drying over anhydrous magnesium sulfate, filtration and evaporation of the solvent is subjected to chromatography on silica gel (ethyl acetate/hexane 1:5). The product is recrystallized from ethyl acetate/hexane. 21.5 g of the compound are obtained as yellow crystals with a melting point of 117-118° C.

Aufarbeitung

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with 4×250 ml of ethyl acetate
  3. customThe solution so obtained
  4. washis washed with water and afterwards with a saturated solution of sodium chloride
  5. customThe residue which is obtained
  6. dry with materialafter drying over anhydrous magnesium sulfate, filtration and evaporation of the solvent
  7. customThe product is recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b01ce4f9e27840cbb632a703bbf82d46
Quelldatensatz
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06576797B1

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