Potassium Carbonate → Methyl 3-[1-(3-isobutylphenyl)ethyl]benzoate

HRID 249150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249150
O[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH:16]=1)[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:21]([C:17]1[CH:16]=[C:15]([CH:13]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH3:14])[CH:20]=[CH:19][CH:18]=1)[CH:22]([CH3:24])[CH3:23]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 88068Methyl 3-HydroxybenzoateHCID 190248461-(1-Bromoethyl)-3-isobutylbenzene

Produkt 1

HCID 19024733Methyl 3-[1-(3-isobutylphenyl)ethyl]benzoateAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of methyl 3-hydroxybenzoate (939 mg), 1-(1-bromoethyl)-3-isobutylbenzene (1.49 g) and potassium carbonate (1.71 g) in N,N-dimethylformamide (20 ml) was stirred at 25° C. overnight. The mixture was partitioned between ether and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (30 g) eluting with a mixture of ethyl acetate and hexane (1:10) to give methyl 3-[1-(3-isobutylphenyl)ethyl]benzoate (1.45 g) as an oil.

Aufarbeitung

  1. customThe mixture was partitioned between ether and 1N hydrochloric acid
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (30 g)
  7. washeluting with a mixture of ethyl acetate and hexane (1:10)

Quellen und Nachweise

ORD-Eintrag
ord-6f3ac6ae116945d0b3416216a399fa73
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212320

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