Methanol → Benzoic acid, 3-ethyl-

HRID 732003

Reaktionsgleichung

Reaktionsgleichung von HRID 732003
[OH-:1].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH3:12])[CH:6]=1)#N.C[OH:14]>>[CH2:11]([C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:3]([OH:14])=[O:1])[CH3:12]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 96692Benzonitrile, 3-ethyl-

Produkt 1

HCID 96207Benzoic acid, 3-ethyl-Ausbeute 28 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

6 M Sodium hydroxide (25 ml) was added to 1-cyano-3-ethylbenzene (1 g, 7.62 mmol) in methanol (25 ml) and then heated at 100° C. overnight. After concentrating the reaction mixture, the aqueous layer was washed with dichloromethane (2×), then acidified pH about 3 with 12 M HCl. The precipitate was extracted with ethyl acetate then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 3-ethylbenzoic acid as a colorless oil; 0.770 g (28% yield over 2 steps). 1H NMR (CDC13), δ (ppm): 7.76 (d, 2H), 7.43 (m, 2H), 2.67 (m, 2H), 1.19 (t, 3H).

Aufarbeitung

  1. concentrationAfter concentrating the reaction mixture
  2. washthe aqueous layer was washed with dichloromethane (2×)
  3. extractionThe precipitate was extracted with ethyl acetate
  4. washthen washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d63e18e9f54945b9a3f8f033d1456c34
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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