Nitric Acid → Ethyl 5-chloro-2-nitro-4-trifluoromethylcinnamate

HRID 487349Notes

Reaction equation

HRID 487349 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[C:15]([F:18])([F:17])[F:16])[CH:5]=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].S(=O)(=O)(O)O.[N+:24]([O-])([OH:26])=[O:25]>O>[Cl:1][C:2]1[C:14]([C:15]([F:16])([F:17])[F:18])=[CH:13][C:12]([N+:24]([O-:26])=[O:25])=[C:4]([CH:3]=1)[CH:5]=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 53835929Ethyl 3-chloro-4-trifluoromethylcinnamate

Product 1

HCID 53647385Ethyl 5-chloro-2-nitro-4-trifluoromethylcinnamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 100 mg of ethyl 3-chloro-4-trifluoromethylcinnamate and 1.8 ml of concentrated sulfuric acid was added 42 ml of 60% nitric acid at -15° C. After stirring at the same temperature for a few minutes, the reaction mixture was poured into a cold water, and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated. The residue was purified by a silica gel column chromatography to give 102 mg of ethyl 5-chloro-2-nitro-4-trifluoromethylcinnamate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customevaporated
  5. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-a78398556a6c45d3b1a2b4a426cea39c
Source dataset
uspto-grants-1994_03
Patent number
US05294718

Reaction notes

Loading…