Acetone → 2,4-Pentanedione, 1-phenyl-

HRID 85540

Reaktionsgleichung

Reaktionsgleichung von HRID 85540
[C:1]1([CH2:7][C:8]([O:10]CC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][C:14]([CH3:16])=[O:15].Cl>CCOCC>[C:1]1([CH2:7][C:8](=[O:10])[CH2:13][C:14](=[O:15])[CH3:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 7590Ethyl phenylacetate

Produkt 1

HCID 187232,4-Pentanedione, 1-phenyl-Ausbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of NaNH2 (19.02 g, 480 mmol) in anhydrous ether (400 mL) under N2 at −5° C. was added dropwise ethyl phenylacetate (19.2 g, 150 mmol) and then acetone (21.23 g, 370 mmol) with vigorous stirring. After addition, the reaction mixture was stirred at room temperature overnight. The mixture was then acidified to pH 4.0-5.0 with 1N HCl. The organic layer was separated and concentrated in vacuo. The crude product was purified by silica gel chromatography to give 1-phenyl-2,4-pentanedione (18.32 g, 44%). 1H NMR (400 MHz, CDCl3-d3) δ 15.49 (br s, 1H), 7.33-7.45 (m, 5H), 5.53 (s, 1H), 3.66 (s, 2H), 2.10 (s, 3H).

Aufarbeitung

  1. additionAfter addition
  2. customThe organic layer was separated
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f1e8708eb6a5409d80fa92e0a14430f7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846935B2

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