Hydrochloric Acid → 2-(4-(Trifluoromethyl)phenyl)propanoic acid

HRID 1464194

Reaktionsgleichung

Reaktionsgleichung von HRID 1464194
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C(O)C>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH3:15])[C:10]([OH:12])=[O:11])=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15062351Ethyl 2-(4-(trifluoromethyl)phenyl)propanoate

Produkt 1

HCID 102424842-(4-(Trifluoromethyl)phenyl)propanoic acidAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1.93 g (7.8 mmol) of ethyl 2-(4-[trifluoromethyl]phenyl)propionate, 10 mL of 1N NaOH, and 10 mL of absolute ethanol was heated to reflux for 3 hours, allowed to cool to room temperature, and poured into 50 mL of 1N HCl. The resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers afforded an oil which was crystallized from hexanes to give 0.90 g (50% yield) of the acid as a white, crystalline solid: mp 56°-58° C.; 1H NMR (CDCl3) 1.47 (d, 3H, J=7 Hz), 3.73 (q, 1H, J=7 Hz), 7.36 (d, 2H, J=8 Hz), 7.52 (d, 2H, J=8 Hz); 19F NMR (CDCl3, relative to CFCl3)-63.2 ppm (s); IR (neat) 2963, 1712, 1619, 1419, 1327, 1264, 1232, 1166, 1124, 1072, 1019, 843 cm-1.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. extractionThe resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane
  4. dry with materialCombination, drying (MgSO4), and concentration of the organic layers
  5. customafforded an oil which
  6. customwas crystallized from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e93fe74613294760b335087328a20cb5
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05302752

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