Trifluoroacetic acid → 2,3-Dihydro-6-hydroxy-3-phenylinden-1-one

HRID 331260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 331260
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:17])/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:9][C:8]2=[O:17])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 5356382T5637827

Produkt 1

HCID 703075012,3-Dihydro-6-hydroxy-3-phenylinden-1-oneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(E)-1-(3-Hydroxyphenyl)-3-phenylprop-2-en-1-one (48.7 g, 217 mmol) obtained in Step 1 and CF3COOH (161 mL, 10 eq) were placed into a flask and stirred for 24 h at 80° C. After cooling to room temperature, toluene (200 mL) was added and the solution was concentrated to remove TFA under reduced pressure. The residue was dissolved in EtOAc, washed with H2O, dried over MgSO4, and concentrated in vacuo to obtain the desired product (48.0 g, 99%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solution was concentrated
  3. customto remove TFA under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c6278b364d5449678b2c237d922c7ead
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877747B2

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