Nitroethane → 2,4-Dihydroxybenzonitrile

HRID 411848

Reaktionsgleichung

Reaktionsgleichung von HRID 411848
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C([O-])(=O)C.[Na+].[N+:16](CC)([O-])=O>C(O)(=O)C>[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:16]

Komponenten

5

Edukt 3

HCID 6587NitroethaneHCID 72132,4-DihydroxybenzaldehydeHCID 517045Sodium Acetate

Produkt 1

HCID 30175202,4-DihydroxybenzonitrileAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 2,4-dihydroxybenzaldehyde (5.0 g, 36.2 mmol), sodium acetate (5.94 g, 72.4 mmol), nitroethane (5.44 g, 72.4 mmol) and glacial acetic acid (10 ml) was refluxed for 6 hours. After cooling, the mixture was poured onto ice (100 g) and extracted with ethyl acetate (4×50 ml). The combined organic layers were washed with saturated NaHCO3 until the pK of the aqueous layer remained at 8, dried (Na2SO4) and the solvent removed in vacuo. Flash chromatography (SiO2, cyclohexane: ethyl acetate=1:1) afforded 2,4-dihydroxybenzonitrile (2.87 g, 59%) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ6.33 (d, 1 H, J=8.6 Hz), 6.43 (s, 1 H), 7.37 (d, 1 H, J=8.6 Hz), 10.35 (s, 1 H), 10.78 (s, 1 H). IR (KBr) 2200 cm−1.

Aufarbeitung

  1. temperaturewas refluxed for 6 hours
  2. temperatureAfter cooling
  3. additionthe mixture was poured onto ice (100 g)
  4. extractionextracted with ethyl acetate (4×50 ml)
  5. washThe combined organic layers were washed with saturated NaHCO3 until the pK of the aqueous layer
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c97384395cba41f795ee1ce6585c05d6
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559315B1

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