Propionic Acid → 1,4-Naphthalenedione,2-ethyl-

HRID 654845Notes

Reaction equation

HRID 654845 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[C:13](O)(=O)[CH2:14]C.S1(CCCC1)(=O)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.O.[N+]([O-])([O-])=O.[Ag+]>[CH2:13]([C:3]1[C:4](=[O:11])[C:5]2[C:10]([C:1](=[O:12])[CH:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:14]

Participants

8

Reactant 4

HCID 1032Propionic AcidHCID 85301,4-NaphthoquinoneHCID 31347SulfolaneHCID 62648Ammonium Persulfate

Product 1

HCID 949221,4-Naphthalenedione,2-ethyl-

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,4-naphthoquinone (7.91 g), propanoic acid (3.70 g) and silver nitrate (1.53 g) in a mixture of acetonitrile (11.4 mL), sulfolane (34.1 mL) and water (79.5 mL) was heated at 60°-65° C. for 2 hours. A solution of ammonium persulfate (13.7 g) in water (25 mL) was then added dropwise. The mixture was cooled in ice water and extracted with ether. The organic layer was washed with saturated sodium bicarbonate, water and brine, then dried, filtered and evaporated. Chromatography over silica gel afforded 2-ethyl-1,4-naphthoquinone, m.p. 87°-88° C.

Workup

  1. temperaturewas heated at 60°-65° C. for 2 hours
  2. extractionextracted with ether
  3. washThe organic layer was washed with saturated sodium bicarbonate, water and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d9b6c0a0a142436e8c9a681adf8ae6e0
Source dataset
uspto-grants-1992_07
Patent number
US05134161

Reaction notes

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