Hydrochloric Acid → 1,1-Diphenylacetone

HRID 864493

Reaktionsgleichung

Reaktionsgleichung von HRID 864493
FC(F)(F)C1C=[C:5]([CH2:13][O:14]CC#N)C=C(C(F)(F)F)C=1.[Li][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([Li])CCC.C1(CC2C=CC=CC=2)C=CC=CC=1.Cl>CCCCCC.C(OCC)C.C(OCC)(=O)C>[C:22]1([CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:13](=[O:14])[CH3:5])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 7580DiphenylmethaneHCID 19049342((3,5-Bis(trifluoromethyl)phenyl)methyloxy)acetonitrileHCID 178418339ButyllithiumHCID 178506892HCID 178506892, Verbindung

Produkt 1

HCID 699071,1-Diphenylacetone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a cooled (-80° C.) solution of ((3,5-bis(trifluoromethyl)phenyl)methyloxy)acetonitrile (0.51 g; Example 1a, Method B(i) was added 0.42M lithio diphenylmethane (10 ml; prepared by addition of 2.5M n-butyl lithium in hexane (10 ml) to a cooled (-80° C.) solution of diphenylmethane (4.2 g) in diethyl ether (5 ml), followed by warming to room temperature for 3 hours). The solution was warmed to room temperature for 0.5h and then 1M-hydrochloric acid (10 ml) and ethyl acetate were added and the organic phase washed with saturated brine and dried (MgSO4). After evaporation in vacuo the residue was chromatographed on silica gel (eluting with 5% ethyl acetate in hexane ) to give 1-(3,5-bis(triflouromethyl)phenyl)methyloxy)-3,3-diphenyl acetone as an oil which gave an identical 1H NMR spectrum to the material prepared by Method A.

Aufarbeitung

  1. washthe organic phase washed with saturated brine
  2. dry with materialdried (MgSO4)
  3. customAfter evaporation in vacuo the residue
  4. customwas chromatographed on silica gel (eluting with 5% ethyl acetate in hexane )

Quellen und Nachweise

ORD-Eintrag
ord-5043b7a381d4458fbaf08ecf3dc97c9c
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563161

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