Water → 2-Ethoxy-4-(trifluoromethyl)benzonitrile

HRID 1167300Notes

Reaction equation

HRID 1167300 reaction equation
[N+]([C:4]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.[O-:16][CH2:17][CH3:18].[Na+].O>C(O)C>[CH2:17]([O:16][C:4]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 699022-Nitro-4-(trifluoromethyl)benzonitrileHCID 2723922Sodium ethoxide

Product 1

HCID 450943912-Ethoxy-4-(trifluoromethyl)benzonitrileYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-nitro-4-trifluoromethyl-benzonitrile (4.052 g, 18 mmol) in ethanol (25 mL) were added sodium ethoxide solution (13.4 mL, 36 mmol, 21% wt in ethanol) dropwise over 30 min. The reaction mixture was stirred at room temperature for 1 h. Water (50 mL) was added and the resulting mixture was stirred for 15 min. The solid was filtered off, washed with water and dried under vacuum for 3 d to give 2-ethoxy-4-trifluoromethyl-benzonitrile as a beige solid (2.85 g, 74%). It was used without further purification.

Workup

  1. stirringthe resulting mixture was stirred for 15 min
  2. filtrationThe solid was filtered off
  3. washwashed with water
  4. customdried under vacuum for 3 d

Sources & evidence

ORD record
ord-a8ecd1ac6729488aaa017533ae9a90d2
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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