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

HRID 31505

Reaction equation

HRID 31505 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 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-nitro-4-trifluoromethyl-benzonitrile (71.7 g, 318.5 mmol) in anhydrous ethanol (400 mL) at room temperature was added sodium ethoxide (238 mL, 637 mmol, 21% solution in ethanol) dropwise over a period of 30 min. The reaction mixture was stirred at room temperature for 1 h. Water (1 L) was added, and the mixture was stirred for 15 min. The solids were filtered off, washed with water, and dried in the vacuum oven (40° C.) overnight to give 2-ethoxy-4-trifluoromethyl-benzonitrile (64 g, 93% yield).

Workup

  1. stirringthe mixture was stirred for 15 min
  2. filtrationThe solids were filtered off
  3. washwashed with water
  4. customdried in the vacuum oven (40° C.) overnight

Sources & evidence

ORD record
ord-886762afd6f6426590df8ef0b9b3949e
Source dataset
uspto-grants-2008_09
Patent number
US07425638B2

Linked notes

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