Ethanol → Cinnamoylbenzene

HRID 858766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 858766
CO[C:3]1[CH:10]=[C:9](OC)[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[CH:13]1([C:18]([CH3:20])=O)[CH2:17][CH2:16][CH2:15][CH2:14]1.[OH-].[Na+].[CH2:23](O)C>>[C:13]1([CH:18]=[CH:20][C:5]([C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:3]=2)=[O:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:23]=1

Komponenten

5

Edukt 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 22326Cyclopentyl methyl ketoneHCID 691752,4-Dimethoxybenzaldehyde

Produkt 1

HCID 7189Cinnamoylbenzene

Versuchsvorschrift

A solution of 2,4-dimethoxybenzaldehyde (10.27 g, 45 mmol) and methyl cyclopentyl ketone (6.06 g, 54 mmol) in anhydrous ethanol (81 mL) was treated with 5 M NaOH (aq) (18 mL, 90 mmol) and the mixture stirred at room temperature for 18 h. The volatiles were removed in vacuo. The residue was extracted with ether (100 mL) and the extract washed with water (3×60 mL), then with brine. The ethereal solution was dried over MgSO4, filtered, and concentrated in vacuo, affording the intermediate chalcone in a crude yield of 14.63 g. The crude intermediate (14.52 g) was dissolved in 110 mL ethyl acetate, treated with platinum oxide (5 mole %) and stirred over 1 atm of H2 at room temperature overnight. The Pt was filtered through a fine fritted funnel and the black residue washed with ethyl acetate. The filtrate was concentrated in vacuo to give a yellowish resin. The resin was chromatographed using silica gel and 6:1 hexanes/ethyl acetate, yielding 6.02 g (41%) of the ketone as a colorless oil.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. extractionThe residue was extracted with ether (100 mL)
  3. washthe extract washed with water (3×60 mL)
  4. dry with materialThe ethereal solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-75a3a444f63b4a71b56976ad3e43a300
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148226B2

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