Sulfuric Acid → HCID 178450759, compound

HRID 1289862Notes

Reaction equation

HRID 1289862 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].[C:5]1([N:11]2[C:15]([OH:16])=[CH:14][C:13]([C:17]([OH:19])=[O:18])=[N:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.S(=O)(=O)(O)O.[OH-].[Na+]>O1CCOCC1>[C:5]1([N:11]2[C:15]([OH:16])=[CH:14][C:13]([C:17]([O:19][C:2]([CH3:3])([CH3:1])[CH3:4])=[O:18])=[N:12]2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 14798Sodium HydroxideHCID 178524628HCID 178524628, compound

Product 1

HCID 178450759HCID 178450759, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
-78 °C

Procedure

To condensed isobutylene (1 ml) in a resealable glass tube was added 1-phenyl-3-carboxy-5-hydroxypyrazole (1 g; 4.9 mmol) in 30 ml of dioxane. The reaction mixture was cooled to -78° C. and 0.5 ml of conc. sulfuric acid was then added. The tube was sealed, stirred at room temperature for 6 hours, and cooled. The tube was opened, the mixture was neutralized and then basified (pH=12) with 2N NaOH solution, and extracted with ethyl acetate (3×). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo to afford 431 mg of 1-phenyl-3-(t-butyloxycarbonyl)-5-hydroxypyrazole as a white solid.

Workup

  1. customThe tube was sealed
  2. temperaturecooled
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4e51f863f0949cd82125dd140f673a9
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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