p-Toluenesulfonic acid monohydrate → 4-Chloro-1-(m-tolyl)butan-1-one

HRID 1620991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620991
[CH:1]1([C:4]([C:6]2[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=2)=[O:5])[CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.O.[ClH:25].N1C=CC=CC=1>CC#N.C(OCC)(=O)C>[Cl:25][CH2:3][CH2:2][CH2:1][C:4]([C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1)=[O:5]

Komponenten

6

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 10176127Pyridinium chlorideHCID 21431776Cyclopropyl 3-methylphenyl ketone

Produkt 1

HCID 215346004-Chloro-1-(m-tolyl)butan-1-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of Example 91A (2.56 g, 16.9 mmol), TsOH.H2O (3.2 g, 16.9 mmol) and pyridine hydrochloride (3.88 g, 33.8 mmol) in CH3CN (60 mL) was heated at 160° C. for 3 hours under microwave and the CH3CN was removed by reduced pressure to give a residue, which was re-dissolved in ethyl acetate (100 mL). The resulting organic solution was washed with aqueous NaHCO3 (50 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated to give a black oil. The oil was purified by chromatography on silica gel column (petroleum ether:ethyl acetate=20:1) to give the title compound (1.56 g, 50%). LC-MS (M+H): m/z 197. 1H NMR (400 MHz, CDCl3): δ ppm 7.765-7.786 (m, 2H), 7.354-7.397 (m, 2H), 3.679 (t, J=6.2 Hz, 2H), 3.170 (t, J=6.2 Hz, 2H), 2.419 (s, 3H), 2.194-2.260 (m, 2H).

Aufarbeitung

  1. customthe CH3CN was removed by reduced pressure
  2. customto give a residue, which
  3. washThe resulting organic solution was washed with aqueous NaHCO3 (50 mL) and brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a black oil
  8. customThe oil was purified by chromatography on silica gel column (petroleum ether:ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-2ab1eaa85e6d4909b2daca9e7bc65180
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772500B2

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