Phenol → HCID 67333442, Verbindung

HRID 1669642

Reaktionsgleichung

Reaktionsgleichung von HRID 1669642
[F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][C:6]([C:15]2[CH:16]=[CH:17][C:12]([OH:18])=[CH:13][CH:14]=2)([C:15]2[CH:16]=[CH:17][C:12]([OH:18])=[CH:13][CH:14]=2)[CH2:5][CH2:4]1

Komponenten

6

Edukt 2

HCID 996PhenolHCID 27774914-(Trifluoromethyl)cyclohexanone

Produkt 1

HCID 67333442HCID 67333442, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of 4-(trifluoromethyl)cyclohexanone (1.13 g, 6.8 mmol) and phenol (2.01 g, 21.4 mmol) in 3 mL of concentrated HCl (aq) was stirred at 40° C. for 18 h. The reaction mixture was diluted with EtOAc and saturated aqueous NaHCO3 was slowly added. The organic layer was collected and the aqueous layer was extracted twice with EtOAc. The combined organic layers were concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with a gradient of 0% to 40% EtOAc/hexanes over 10 column volumes, then 40% to 100% EtOAc/hexanes over 5 column volumes, affording the title compound as a white solid.

Aufarbeitung

  1. additionwas slowly added
  2. customThe organic layer was collected
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. concentrationThe combined organic layers were concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel eluting with a gradient of 0% to 40% EtOAc/hexanes over 10 column volumes

Quellen und Nachweise

ORD-Eintrag
ord-66dcd8f751764dc8aef01be8a59c9e70
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989472B2

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