Hydrochloric Acid → N-(2-Hydroxy-4-octyloxy-phenyl)-2,2,2-trifluoro-acetamide

HRID 18447

Reaktionsgleichung

Reaktionsgleichung von HRID 18447
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].Cl>CN(C=O)C>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:15])[C:11]([F:12])([F:13])[F:14]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 18454996N-(2,4-dihydroxyphenyl)-2,2,2-trifluoro-acetamide

Produkt 1

HCID 58685869N-(2-Hydroxy-4-octyloxy-phenyl)-2,2,2-trifluoro-acetamideAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-(2,4-dihydroxy phenyl)-2,2,2-trifluoro-acetamide (0.44 g; 2 mmol) in DMF (4 mL) was added K2CO3 and 1-bromooctane (0.37 mL; 2.1 mmol). The slurry was stirred for 2 days at room temperature, poured onto 0.1 M HCl (aq.; 50 mL) and then extracted with diethylether (30 mL). The organic phase was dried (MgSO4), filtered and the eluate evaporated to leave 550 mg of black solid which was purified by chromatography (SiO2; PE80-100° C./EtOAc=4:1) to leave 100 mg (15%) of a pure white solid. Mp. 114-116° C.; MS (GC-MS; Cl): 334 (MH+).

Aufarbeitung

  1. extractionextracted with diethylether (30 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customthe eluate evaporated

Quellen und Nachweise

ORD-Eintrag
ord-4ee9517eb9ec420cb4980422cdb446dd
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741352B2

Verknüpfte Notizen

Wird geladen…