Nitric Acid → 1,1,1,3,3,3-hexafluoro-2-(3-nitrophenyl)propan-2-ol

HRID 1442815Notes

Reaction equation

HRID 1442815 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[N+:17]([O-])([OH:19])=[O:18]>OS(O)(=O)=O>[F:1][C:2]([F:15])([F:16])[C:3]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([N+:17]([O-:19])=[O:18])[CH:14]=1)([OH:8])[C:4]([F:6])([F:5])[F:7]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 69748alpha,alpha-Bis(trifluoromethyl)benzyl alcohol

Product 1

HCID 2795821,1,1,3,3,3-hexafluoro-2-(3-nitrophenyl)propan-2-olYield 87.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

1,1,1,3,3,3-Hexafluoro-2-phenylpropan-2-ol (6.1 g, 25 mmol) was dissolved in concentrated H2SO4 (15 mL) and cooled to −10° C. HNO3 (90%, 5 mL, 100 mmol) was added dropwise and the temperature was maintained below −5° C. The mixture was stirred at −5° C. for 10 min and was poured into ice. The precipitate was collected via filtration, washed with ice water until pH˜6, and was dried to yield 1,1,1,3,3,3-hexafluoro-2-(3-nitrophenyl)propan-2-ol (6.3 g) that was used in next step without further purification.

Workup

  1. temperaturethe temperature was maintained below −5° C
  2. additionwas poured into ice
  3. filtrationThe precipitate was collected via filtration
  4. washwashed with ice water until pH˜6
  5. customwas dried

Sources & evidence

ORD record
ord-bcae7d13792c46d3baef567c3402fec3
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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