Water → 3-Hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrile

HRID 1383303

Reaktionsgleichung

Reaktionsgleichung von HRID 1383303
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH2:10][C:11]#[N:12].[CH:13](OCC)=[O:14].[O-]CC.[Na+].O>C(O)C>[OH:14][CH:13]=[C:10]([C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])[C:11]#[N:12]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8025Ethyl formateHCID 5206982,4,6-TrimethylphenylacetonitrileHCID 2723922Sodium ethoxide

Produkt 1

HCID 701428183-Hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrileAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 2,4,6-trimethylphenylacetonitrile (75 g) and ethyl formate (67 g) in 225 ml absolute ethanol was treated with solid sodium ethoxide (36 g) in small portions over 10 minutes, with good stirring. The mixture was heated to 60° C. under nitrogen for 16 hours and allowed to cool to room temperature. The reaction mixture was poured into 1.2 liters of water, extracted with diethyl ether (3×200 ml). The aqueous phase was acidified with 6M HCl to pH=1 and extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried over MgSO4 and concentrated, yielding 46 g (98%) of 3-hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrile (intermediate 1).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether (3×200 ml)
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-982bb3752ab5436fbe57d48d351bda6f
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255310B1

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