Nitric Acid → HCID 23001766, compound

HRID 398059Notes

Reaction equation

HRID 398059 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=2)[O:3]1.OS(O)(=O)=O.[N+:25]([O-])([OH:27])=[O:26]>>[N+:25]([C:5]1[CH:6]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[C:9]2[C:4]=1[O:3][C:2]([CH3:19])([CH3:1])[CH2:11][C:10]2([CH3:12])[CH3:13])([O-:27])=[O:26]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 12136999HCID 12136999, compound

Product 1

HCID 23001766HCID 23001766, compound

Conditions

Temperature
0 °C

Procedure

Ethyl 2,2,4,4-tetramethyl-6-chromanoate (150 mg, 0.57 mmol) was slowly added to 0.3 ml of conc. H2SO4 at 0° C. To this mixture was added very slowly 0.03 ml of HNO3. The reaction mixture was stirred at 0° C. for 30 min and poured into ice-water. The product was extracted into 5 ml of ethyl acetate, washed with NaHCO3 (sat.), brine and dried over MgSO4. After concentration, the product was purified by column chromatography (ethyl acetate/hexane 1/10) to yield 74 mg of light-yellow oil.

Workup

  1. extractionThe product was extracted into 5 ml of ethyl acetate
  2. washwashed with NaHCO3 (sat.), brine
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentration
  5. customthe product was purified by column chromatography (ethyl acetate/hexane 1/10)

Sources & evidence

ORD record
ord-f8f2268484cb4cd9a5bbd3733d6a61c8
Source dataset
uspto-grants-2003_08
Patent number
US06610744B2

Reaction notes

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