Nitric Acid → HCID 59234954, compound

HRID 1919773Notes

Reaction equation

HRID 1919773 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:22])([C:18]([F:21])([F:20])[F:19])[C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=1[CH2:23][CH2:24][CH3:25].[N+:26]([O-])([OH:28])=[O:27]>>[OH:6][C:7]1[C:8]([CH2:23][CH2:24][CH3:25])=[CH:9][C:10]([C:13]([OH:22])([C:14]([F:15])([F:16])[F:17])[C:18]([F:19])([F:20])[F:21])=[CH:11][C:12]=1[N+:26]([O-:28])=[O:27]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 59201025HCID 59201025, compound

Product 1

HCID 59234954HCID 59234954, compoundYield 16%

Conditions

Temperature
40 °C

Procedure

Concentrated sulfuric acid (1.2 mL) was added to 2-(4-hydroxy-3-propylphenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (500 mg, 1.65 mmol) under ice-cooling. Then, a mixed solution of nitric acid (109 μL) and concentrated sulfuric acid (219 μL) was added dropwise at 30 to 35° C., followed by stirring at 40° C. for three hours. The reaction solution was cooled and then added dropwise to ice water. After neutralization to pH 7 with a sodium hydroxide solution (1 mol/L), the neutralized solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 94.3 mg of the title compound (yield: 16%) as a red orange oil.

Workup

  1. temperaturecooling
  2. temperatureThe reaction solution was cooled
  3. concentrationAfter neutralization to pH 7 with a sodium hydroxide solution (1 mol/L), the neutralized solution was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-2aa9ad5469c04ab1b0a47234ac2adbcb
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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