Nitroethane → 2,4-Diethoxybenzonitrile

HRID 1582475Notes

Reaction equation

HRID 1582475 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[CH:8][C:5]=1[CH:6]=O)[CH3:2].C([O-])(=O)C.[Na+].[N+:20](CC)([O-])=O>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[CH:8][C:5]=1[C:6]#[N:20])[CH3:2]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 517045Sodium AcetateHCID 5864562,4-Diethoxybenzaldehyde

Product 1

HCID 227211912,4-DiethoxybenzonitrileYield 38%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2,4-diethoxybenzaldehyde (5.0 g, 25.7 mmol), sodium acetate (4.23 g, 51.6 mmol), nitroethane (3.86 g, 51.4 mmol) in acetic acid (7 mL) was heated at reflux for 6 h. The mixture was then cooled and poured onto ice-water. The solids were filtered off, washed with water and dried. Chromatography of the residue over silica gel using 2-5% ethyl acetate in hexanes followed recrystallization in ethyl acetate gave 2,4-diethoxybenzonitrile (1.86 g, 38%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. temperatureThe mixture was then cooled
  4. additionpoured onto ice-water
  5. filtrationThe solids were filtered off
  6. washwashed with water
  7. customdried
  8. customrecrystallization in ethyl acetate

Sources & evidence

ORD record
ord-f57c5b7c54d144528a7700309f2b1396
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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