Nitric Acid → 2-Nitro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid

HRID 4745Notes

Reaction equation

HRID 4745 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[N+:22]([O-])([OH:24])=[O:23].O>S(=O)(=O)(O)O>[N+:22]([C:11]1[CH:10]=[C:9]([C:3]([OH:8])([C:4]([F:6])([F:5])[F:7])[C:2]([F:20])([F:21])[F:1])[CH:14]=[CH:13][C:12]=1[CH2:15][CH2:16][C:17]([OH:19])=[O:18])([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 962WaterHCID 15586902HCID 15586902, compound

Product 1

HCID 140766502-Nitro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 63.2 g (0.20 mole) of 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid in 160 ml of concentrated sulfuric acid is added 40 ml of fuming nitric acid (90%) dropwise with stirring at 0°-5°. Following the nitric acid addition the solution is allowed to warm to 20° with stirring over a 1-hour period. The solutionis then added to a mixture of ice and water and allowed to stand for 18 hours. A precipitate results and is filtered, washed with water and dissolved in ether to obtain a solution which is washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated to give a residual solid. The residual solid is recrystallized from chlorobutane to give 40 g of 2-nitro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid having a melting point of 115°-116°.

Workup

  1. temperatureto warm to 20°
  2. stirringwith stirring over a 1-hour period
  3. customA precipitate results
  4. filtrationis filtered
  5. washwashed with water
  6. dissolutiondissolved in ether
  7. customto obtain a solution which
  8. washis washed with water
  9. dry with materialdried with anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customto give a residual solid
  13. customThe residual solid is recrystallized from chlorobutane

Sources & evidence

ORD record
ord-faaf68394c7640afbc0442dba1d6486f
Source dataset
uspto-grants-1988_02
Patent number
US04727180

Reaction notes

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