Sodium Iodide → Benzoic acid, 2-[(4-chlorophenyl)thio]-

HRID 839295

Reaktionsgleichung

Reaktionsgleichung von HRID 839295
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[I-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([SH:20])=[CH:16][CH:15]=1.[OH-].[Na+]>O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 7815p-ChlorothiophenolHCID 83742-Chlorobenzoic AcidHCID 14798Sodium Hydroxide

Produkt 1

HCID 80942Benzoic acid, 2-[(4-chlorophenyl)thio]-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a well stirred mixture of 15.7 g. (0.1 mole) of 2-chlorobenzoic acid and 15.0 g. (0.1 mole) of sodium iodide in 250 ml. of 4-chlorothiophenol was rapidly added a solution of 16 g. (0.4 mole) of sodium hydroxide dissolved in 16 ml. of water. The reaction mixture was heated and concentrated under reduced pressure to an internal temperature of about 145° C. to remove the water and some excess 4-chlorothiophenol. The residue was then stirred at 170° C. for about 7 hours, cooled and diluted with 250 ml. of water. The solution was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extractions were washed with water, dried with magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from a benzene-hexane mixture to give 2-(4'-chlorothiophenoxy)benzoic acid having a melting point of 239°-240° C.

Aufarbeitung

  1. additionmixture of 15.7 g
  2. temperatureThe reaction mixture was heated
  3. concentrationconcentrated under reduced pressure to an internal temperature of about 145° C.
  4. customto remove the water
  5. stirringThe residue was then stirred at 170° C. for about 7 hours
  6. temperaturecooled
  7. additiondiluted with 250 ml
  8. extractionextracted with ethyl acetate
  9. extractionThe ethyl acetate extractions
  10. washwere washed with water
  11. dry with materialdried with magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was recrystallized from a benzene-hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-15d4c09e99044236b30981b8cc34ed3d
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04094900

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