Methanol → Benzoic acid, 3-ethyl-

HRID 273090

Reaktionsgleichung

Reaktionsgleichung von HRID 273090
[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 (CDCl3), 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-cd7af4a827414338a757492d00557d45
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456200B2

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