Ethanol → 3-Methyl-4-(oxetan-3-YL)benzoic acid

HRID 1405393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1405393
[CH3:1][C:2]1[CH:3]=C([CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:13][O:12][CH2:11]1)C#N.[OH-:14].[Na+].[CH2:16]([OH:18])[CH3:17]>>[CH3:1][C:2]1[CH:3]=[C:17]([CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:13][O:12][CH2:11]1)[C:16]([OH:14])=[O:18]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 681533093-Methyl-4-(oxetan-3-YL)benzonitrile

Produkt 1

HCID 681533343-Methyl-4-(oxetan-3-YL)benzoic acidAusbeute 14 %

Versuchsvorschrift

To 3-methyl-4-(oxetan-3-yl)benzonitrile (500 mg, 2.89 mmol) in ethanol (7.5 mL) was added NaOH (3.0 mL of 5 M, 15 mmol) and the mixture immersed in a 85° C. oil bath. The mixture was heated and stirred for 1 h, concentrated, then diluted with ethyl acetate (20 mL). 6N HCl (˜3 mL) was added to adjust pH to 6. The aqueous layer was extracted with ethyl acetate (2×20 mL), then the combined organics washed with brine (10 mL), dried over MgSO4 and concentrated to give a white solid, which was triturated with ether to give a mixture (2:3 by NMR) of acid 3-methyl-4-(oxetan-3-yl)benzoic acid (500 mg, 14%) and amide. ESI-MS m/z calc. 192.2, found 193.3 (M+1)+; Retention time: 0.87 minutes (3 min run).

Aufarbeitung

  1. customimmersed in a 85° C.
  2. temperatureThe mixture was heated
  3. concentrationconcentrated
  4. additiondiluted with ethyl acetate (20 mL)
  5. addition6N HCl (˜3 mL) was added
  6. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  7. washthe combined organics washed with brine (10 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customto give a white solid, which
  11. customwas triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-14c591baf8314e9982b981f0ceb15712
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916565B2

Notizen zur Reaktion

Wird geladen…