Ethyl Acetate → 1-(3,5-Di-t-butylphenyl)butan-1-one

HRID 863383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 863383
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]([OH:19])[CH2:16][CH2:17][CH3:18])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CCOC(C)=O>C(Cl)Cl.O=[Mn]=O>[C:1]([C:5]1[CH:6]=[C:7]([C:15](=[O:19])[CH2:16][CH2:17][CH3:18])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 187050951-(3,5-Di-t-butylphenyl)butan-1-ol

Produkt 1

HCID 187050871-(3,5-Di-t-butylphenyl)butan-1-oneAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 2.37 g (9.05 mmol) of alcohol 19 in 18 mL of CH2Cl2 was added 7.86 g (90.45 mmol) of MnO2. The reaction mixture was stirred for 3 h, then filtered (celite over silica gel pad) and the pad was washed repeatedly with 20 mL aliquots of CH2Cl2. After concentration, ketone 20 was purified by chromatography (SiO2, 3% EtOAc-hexanes) to give 941 mg (3.62 mmol) of 20 (40% yield 1 Hz TLC (10% EtOAc-90% hexanes) Rf 0.7; 1H-NMR (CDCl3) δ1.01 (t, 3H, CH2CH3), 1.34 (s, 18H, 6(CH3)), 1.78 (m, 2H, CH2CH3), 2.96 (t, J=7 Hz, 2H, CH2CH2CH3), 7.63 (t, J=1 Hz, 1H, Ar-H), 7.83 (d, J=1 Hz, 2H, Ar-H).

Aufarbeitung

  1. filtrationfiltered (celite over silica gel pad)
  2. washthe pad was washed repeatedly with 20 mL aliquots of CH2Cl2
  3. concentrationAfter concentration, ketone 20
  4. customwas purified by chromatography (SiO2, 3% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1de789c184a5428e9d2ba7f3177c9e9d
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05721103

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