Sulfuric Acid → HCID 69645905, Verbindung

HRID 10701Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 10701
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH2:9]([O:11][C:12](=[O:22])[C:13]([CH3:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])[CH3:10].S(=O)(=O)(O)O>C(=S)=S>[CH2:9]([O:11][C:12](=[O:22])[C:13]([C:15]1[CH:20]=[CH:19][C:18]([C:5](=[O:7])[CH3:6])=[CH:17][CH:16]=1)([CH3:21])[CH3:14])[CH3:10]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 6367Acetyl chlorideHCID 232036Benzeneacetic acid, alpha,alpha-dimethyl-, ethyl esterHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 69645905HCID 69645905, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel

Versuchsvorschrift

Ex-77A: To a mixture of aluminum chloride (2.8 g, 20.8 mmol) in carbon disulfide (50 mL) was added acetyl chloride (0.74 mL, 10.4 mmol) followed by addition of 2-methyl-2-phenyl-propionic acid ethyl ester (1.0 g, 5.2 mmol). The reaction mixture was refluxed for 2 hours and then poured into ice containing sulfuric acid (6M). The mixture was partitioned. The aqueous layer was extracted with ethyl acetate. The solution of ethyl acetate was washed with hydrochloric acid (0.5M), saturated solution of sodium bicarbonate and brine, dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography. Elution with ethyl acetate (33%, v/v, in hexane) gave 2-(4-acetyl-phenyl)-2-methyl-propionic acid ethyl ester (0.57 g, 47%). 1H NMR (CDCl3) δ 7.92 (d, J=7.6 Hz, 2H), 7.42 (d, J=7.6 Hz, 2H), 4.13 (q, J=7.2 Hz, 2H), 2.59 (s, 3H), 1.61 (s, 3H), 1.59 (s, 3H), 1.18 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. additionpoured into ice
  3. customThe mixture was partitioned
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe solution of ethyl acetate was washed with hydrochloric acid (0.5M), saturated solution of sodium bicarbonate and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography
  9. washElution with ethyl acetate (33%, v/v, in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c553383d655040c5aa6f9fdb97a2ab62
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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