Dimethyl Sulfate → Methyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetate

HRID 411909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 411909
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)=[O:6].[C:19](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(#N)C>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([O:16][CH3:19])=[O:15])=[CH:9][CH:8]=1)=[O:6]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 109235672-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acid

Produkt 1

HCID 10062338Methyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetateAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Mix 2-[4-(4-chloro-butyryl)-phenyl]-2-methyl-propionic acid (10.0 g, 37.3 mmol) and anhydrous potassium carbonate (3.5 g, 25.3 mmol). Heat to 40° C. in acetonitrile (100 mL) and stir under a nitrogen atmosphere. Add dimethyl sulfate (13.3 g, 105 mmol) and reflux for 45 minutes. Evaporate the solvent in vacuo, dissolve the residue in ethyl acetate (50 mL) and wash with water (4×50 mL). Dry (MgSO4), filter through silica gel and evaporate the solvent in vacuo to give the title compound (6.4 g, 89%).

Aufarbeitung

  1. customEvaporate the solvent in vacuo
  2. dissolutiondissolve the residue in ethyl acetate (50 mL)
  3. washwash with water (4×50 mL)
  4. dry with materialDry (MgSO4)
  5. filtrationfilter through silica gel
  6. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-53334f5c96164dc5b783497e3aba4413
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559312B2

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