Methanol → 2-Methoxy-4-(trifluoromethyl)benzonitrile

HRID 2259610Notes

Reaction equation

HRID 2259610 reaction equation
[CH3:1][O-:2].[Na+].CO.[N+]([C:9]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])([O-])=O>O>[CH3:1][O:2][C:9]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 699022-Nitro-4-(trifluoromethyl)benzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 190013762-Methoxy-4-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Twenty-five percent sodium methoxide in methanol (24.3 g, 11 mol) was added dropwise to a stirred mixture of 19 g (0.091 mol) 2-nitro-4-(trifluoromethyl)benzonitrile and 100 mL of methanol at 20°-30° C. After 1 hour at 25° C., 100 mL of water was added. The solids were collected on a filter and washed with water. The solids were dried to yield 12.5 g of product melting at 59°-61° C. 1H NMR (CDCl3) δ4.00 (s, 3H), 7.2-7.7 (3H).

Workup

  1. customThe solids were collected on
  2. filtrationa filter
  3. washwashed with water
  4. customThe solids were dried

Sources & evidence

ORD record
ord-9d1e091bdcb6472094ef7389c7178f9c
Source dataset
uspto-grants-1995_12
Patent number
US05474998

Reaction notes

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