Nitric Acid → 4-Methyl-3-nitrobenzotrifluoride

HRID 1769298Notes

Reaction equation

HRID 1769298 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[N+:12]([O-])([OH:14])=[O:13].S(=O)(=O)(O)O>>[CH3:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 802304-Methylbenzotrifluoride

Product 1

HCID 14728854-Methyl-3-nitrobenzotrifluoride

Procedure

4-Trifluoromethyltoluene (12.8 g) was treated at 60°-70° C. with a mixture of concentrated nitric acid (25 ml) and concentrated sulphuric acid (25 ml) for 5 hours. The solution was poured onto ice (0.5 litres) and extracted with ether (3×100ml). The combined ether extracts were washed with water, dried over sodium sulphate, filtered and evaporated to dryness to give 2-methyl-5-trifluoromethylnitrobenzene (14.8 g) as a pale yellow oil.

Workup

  1. additionThe solution was poured onto ice (0.5 litres)
  2. extractionextracted with ether (3×100ml)
  3. washThe combined ether extracts were washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-8fe42dee94ae40adae12cbc8ae6733b7
Source dataset
uspto-grants-1995_01
Patent number
US05380865

Reaction notes

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