Nitric Acid → HCID 19854188, compound

HRID 1649630Notes

Reaction equation

HRID 1649630 reaction equation
[OH:1][C:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][C:4](=[O:15])[C:3]=1[C:16](=[O:19])[CH2:17][CH3:18].[N+:20]([O-])([OH:22])=[O:21]>C(OC(=O)C)(=O)C.C(O)(=O)C>[OH:1][C:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([N+:20]([O-:22])=[O:21])[CH:9]=2)[CH2:6][CH2:5][C:4](=[O:15])[C:3]=1[C:16](=[O:19])[CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 19854198HCID 19854198, compound

Product 1

HCID 19854188HCID 19854188, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent2×

Conditions

Temperature
5 °C

Procedure

3-hydroxy-2-propionyl-4-(4-methylphenyl)cyclohex-2-ene-1-one (1.2 g) in acetic anhydride (3 g) was cooled to 5° C. A solution of fuming nitric acid (0.42 g) in glacial acetic acid (0.3 g) and acetic anhydride (0.3 g) was added dropwise over a period of 5 minutes. After stirring for a further 1 hour at 5° C. and 2 hours at room temperature, the mixture was poured onto ice-water (100 ml). The aqueous solution was extracted with diethyl ether. The extracts were washed with aqueous sodium bicarbonate, dried over magnesium sulphate, filtered and the ether evaporated in vacouo. The residue was purified on a silica gel column using chloroform as eluant to give the title compound (0.5 g) as a yellow oil.

Workup

  1. additionthe mixture was poured onto ice-water (100 ml)
  2. extractionThe aqueous solution was extracted with diethyl ether
  3. washThe extracts were washed with aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe ether evaporated in vacouo
  7. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-d15bf19c02f143c8b19c7142f6a293cb
Source dataset
uspto-grants-1990_05
Patent number
US04921524

Reaction notes

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