Nitric Acid → (E)-3-(1,4-Naphthoquinon-2-yl)-2-methylpropenoic acid

HRID 1527694Notes

Reaction equation

HRID 1527694 reaction equation
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13]C)=[CH:5][C:4]=1/[CH:15]=[C:16](\[CH3:20])/[C:17]([OH:19])=[O:18].[N+]([O-])(O)=O>C(OCC)(=O)C.CC(O)=O>[C:3]1(=[O:2])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[CH:5]=[C:4]1/[CH:15]=[C:16](\[CH3:20])/[C:17]([OH:19])=[O:18]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 46180242(E)-3-(1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoic acid

Product 1

HCID 25235423(E)-3-(1,4-Naphthoquinon-2-yl)-2-methylpropenoic acidYield 58%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Following modified procedures of Shinkawa et al. and Flader et al.16,22 the acid 29a (0.114 g, 0.419 mmol) was dissolved in ethyl acetate (10 mL) at room temperature, then HNO3 (1.0 mL) and AcOH (3 drops) were added at room temperature. The reaction was stirred at room temperature for 4 hours before being diluted with ethyl acetate and washed with brine. The organic layer was dried over MgSO4, filtered, and condensed. The yellow oil was then purified by either flash column chromatography (2:3 Et2O:hexanes 0.5% AcOH) or recrystallization from Et2O/hexanes to afford 30a (0.059 g, 0.24 mmol, 58%) as a yellow solid.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customcondensed
  5. customThe yellow oil was then purified by either flash column chromatography (2:3 Et2O:hexanes 0.5% AcOH) or recrystallization from Et2O/hexanes

Sources & evidence

ORD record
ord-30176d7947294c8989aa202d5ca1a029
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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