Hydrochloric Acid → 3-Cyano-4-isobutylbenzoic acid

HRID 1744518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744518
Cl[O-:2].[Na+].[OH-].[Na+].[C:6]([C:8]1[CH:9]=[C:10]([C:18](=[O:20])C)[CH:11]=[CH:12][C:13]=1[CH2:14][CH:15]([CH3:17])[CH3:16])#[N:7].Cl>CO>[C:6]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[CH2:14][CH:15]([CH3:16])[CH3:17])[C:18]([OH:20])=[O:2])#[N:7]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 222280063'-Cyano-4'-isobutylacetophenoneHCID 23665760Sodium Hypochlorite

Produkt 1

HCID 222281753-Cyano-4-isobutylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Subsequently, 10% aqueous sodium hypochlorite solution (370 ml) containing sodium hydroxide (8 g) and methanol (5 ml) was heated to 60° C. 3′-Cyano-4′-isobutylacetophenone (20 g) was added thereto by portions and the mixture was stirred for 1 h. The reaction mixture was cooled to room temperature and dilute hydrochloric acid was added, which was followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. n-Hexane was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give 3-cyano-4-isobutylbenzoic acid (8.5 g), melting point: 118° C.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionwhich was followed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the solvent was evaporated under reduced pressure
  6. additionn-Hexane was added to the residue
  7. customcrystallization
  8. customThe crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-4c07db60f7244724ad7624ce2f02fc44
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015218B1

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