Methanol → 2-Nitro-4-trifluoromethylanisole

HRID 2166792Notes

Reaction equation

HRID 2166792 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[Na].[CH3:16][OH:17]>>[CH3:16][O:17][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 5360545Sodium

Product 1

HCID 967482-Nitro-4-trifluoromethylanisole

Procedure

4-chloro-3-nitrobenzotrifluoride (112.8 g) in methanol (200 ml) was mixed with a solution of sodium (11.6 g) in methanol (800 ml) and stirred for 2 hours. The mixture was kept overnight and then stirred and heated under reflux for 3 hours. The solution was left overnight, filtered, and the solvent removed. The remaining oil was taken up in ether (500 ml) and washed with water. The ether solution was dried and evaporated to give 4-methoxy-3-nitrobenzotrifluoride (106 g).

Workup

  1. waitThe mixture was kept overnight
  2. stirringstirred
  3. temperatureheated
  4. temperatureunder reflux for 3 hours
  5. waitThe solution was left overnight
  6. filtrationfiltered
  7. customthe solvent removed
  8. washwashed with water
  9. dry with materialThe ether solution was dried
  10. customevaporated

Sources & evidence

ORD record
ord-d8a3f9df5f4e418ebf5e06029a9ac3e4
Source dataset
uspto-grants-1983_06
Patent number
US04388472

Reaction notes

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