Nitroethane → 2,4-Dihydroxybenzonitrile

HRID 2287411Notes

Reaction equation

HRID 2287411 reaction equation
[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]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 72132,4-DihydroxybenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 30175202,4-DihydroxybenzonitrileYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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 pH 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) δ 6.33 (d, 1H, J=8.6 Hz), 6.43 (s, 1H), 7.37 (d, 1H, J=8.6 Hz), 10.35 (s, 1H), 10.78 (s, 1H). IR (KBr) 2200 cm-1.

Workup

  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 pH of the aqueous layer
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b1588b9052774ec3ba8d73b66b07cfcb
Source dataset
uspto-grants-2000_07
Patent number
US06083966

Reaction notes

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