Nitric Acid → HCID 11790811, compound

HRID 1288799Notes

Reaction equation

HRID 1288799 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[N+:14]([O-])([OH:16])=[O:15]>OS(O)(=O)=O>[CH3:7][C:2]([C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)([CH3:1])[CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 13890beta-Phenylisovaleric acid

Product 1

HCID 11790811HCID 11790811, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To cooled (0° C) concentrated H2SO4 (18.5 mL), was added 3-methyl-3- phenylbutanoic acid (10 g, 56 mmol). Next, a cooled solution of HNO3 (3 mL) in H2SO4 (6.2 mL) was added dropwise and the reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 30 min more. The mixture was poured into ice and the resulting solution was allowed to stand in the refrigerator overnight. The precipitate was filtered, washed with H2 0 and dried, to afford a crude product (14.5 g). This was purified by chromatography on silica gel (CHCl3 :MeOH, 3%) to give the title compound (5.9 g, 47%). 1H NMR (80MHz, CDCl3) δ (TMS): 8.16 (d, J=6.5 Hz, 2H), 7.55 (d, J=6.5 Hz, 2H), 3.5 (m, 1H), 2.70 (s, 2H), 1.50 (s, 6H).

Workup

  1. waitat room temperature for 30 min more
  2. additionThe mixture was poured into ice
  3. customto stand in the refrigerator overnight
  4. filtrationThe precipitate was filtered
  5. washwashed with H2 0
  6. customdried
  7. customto afford a crude product (14.5 g)
  8. customThis was purified by chromatography on silica gel (CHCl3 :MeOH, 3%)

Sources & evidence

ORD record
ord-ebe4dad8b9cd44ddb33c360edd9339be
Source dataset
uspto-grants-1998_05
Patent number
US05747477

Reaction notes

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