Hydrochloric Acid → 2-(2,2',4'-Trifluoro-4-biphenylyl)propionic acid

HRID 972354

Reaktionsgleichung

Reaktionsgleichung von HRID 972354
S(O)(O)(=O)=O.NO.C([O-])(=[O:10])C.[Na+].[F:13][C:14]1[CH:19]=[C:18]([CH:20]([CH3:23])[CH:21]=[O:22])[CH:17]=[CH:16][C:15]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31].FC1C=C(C(C)C(N)=O)C=CC=1C1C=CC(F)=CC=1F.[OH-].[Na+].Cl>C(O)C.O.CCOCC.S([O-])([O-])(=O)=O.[Ni+2]>[F:13][C:14]1[CH:19]=[C:18]([CH:20]([CH3:23])[C:21]([OH:10])=[O:22])[CH:17]=[CH:16][C:15]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31]

Komponenten

11

Edukt 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 517045Sodium AcetateHCID 214067542-(2,2',4'-Trifluoro-4-biphenylyl)propionamideHCID 214067562-(2,2',4'-Trifluoro-4-biphenylyl)propionaldehyde

Produkt 1

HCID 203334592-(2,2',4'-Trifluoro-4-biphenylyl)propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24586Nickel SulfateKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Hydroxylamine sulphate (3.02 g.) was added to an aqueous solution of sodium acetate [prepared from glacial acetic acid (2.4 ml.), 18N aqueous sodium hydroxide (2.34 ml.) and water (23 ml.)]. 2-(2,2',4'-Trifluoro-4-biphenylyl)propionaldehyde (8.26 g.) in ethanol (23 ml.) was added and the mixture was stirred at room temperature for 2.5 hours and then at 90° C. for 1 minute. After cooling, the precipitated oxime was suspended in water containing nickel sulphate (0.2 g.) and heated to reflux to obtain an aqueous suspension of 2-(2,2',4'-trifluoro-4-biphenylyl)propionamide. Aqueous sodium hydroxide (18N, 6.75 ml.) was then added and refluxing continued for 24 hours. The resulting solution was cooled to 40° C., acidified with concentrated hydrochloric acid, and the product isolated in ether. After some purification by a conventional back-extraction technique with aqueous potassium carbonate, the final ether extract was evaporated to dryness. This crude acid in methylene chloride was chromatographed on a column of a synthetic magnesia/silica gel adsorbent. Evaporation of the eluate and recrystallisation of the residue from petroleum ether (b.p. 80°-100° C.) gave 2-(2,2',4'-trifluoro-4-biphenylyl)propionic acid, m.p. 105°-108° C.

Aufarbeitung

  1. waitat 90° C. for 1 minute
  2. temperatureAfter cooling
  3. temperatureheated
  4. temperatureto reflux
  5. customto obtain
  6. temperaturerefluxing
  7. waitcontinued for 24 hours
  8. temperatureThe resulting solution was cooled to 40° C.
  9. customAfter some purification
  10. extractionby a conventional back-extraction technique with aqueous potassium carbonate
  11. extractionthe final ether extract
  12. customwas evaporated to dryness
  13. customThis crude acid in methylene chloride was chromatographed on a column of a synthetic magnesia/silica gel adsorbent
  14. customEvaporation of the eluate and
  15. customrecrystallisation of the residue from petroleum ether (b.p. 80°-100° C.)

Quellen und Nachweise

ORD-Eintrag
ord-d8eab87b04c84f34860bb6e995c08577
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04052514

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