Hydrochloric Acid → (R)-3-(3,5-dimethylbenzoyl)-4-methyldihydrofuran-2-one

HRID 1275184

Reaktionsgleichung

Reaktionsgleichung von HRID 1275184
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[CH:5]=1.[OH-].[Na+].Cl.[CH3:16][C@H:17]1[CH2:21][O:20][C:19](=[O:22])[CH2:18]1>>[CH3:10][C:8]1[CH:9]=[C:4]([CH:5]=[C:6]([CH3:11])[CH:7]=1)[C:3]([C@H:18]1[CH:17]([CH3:16])[CH2:21][O:20][C:19]1=[O:22])=[O:12]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 32786Benzoic acid, 3,5-dimethyl-, methyl esterHCID 5325910(R)-4-Methyldihydrofuran-2(3H)-one

Produkt 1

HCID 53860757(R)-3-(3,5-dimethylbenzoyl)-4-methyldihydrofuran-2-oneAusbeute 62,1 %

Versuchsvorschrift

To a solution of (R)-4-methyldihydrofuran-2-one (1.68 g in 40 mL dioxane) were added 5.51 g 3,5-dimethylbenzoic acid methyl ester followed by 1.82 g sodium hydroxide and the mixture heated to reflux on an oil bath. After 3 hours, the mixture was cooled to room temperature and the pH neutralized by the addition of 0.5N hydrochloric acid. The mixture was then extracted with ethyl acetate and the organic portion washed with brine and dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 9:1) gave the title compound (2.42 g).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washthe organic portion washed with brine
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-808dbf4b11fe495da1217bf9fe0af74f
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06159989

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