2-Methoxy-1,4-Naphthoquinone → 2-Methoxy-1,4-diacetyloxynaphthalene

HRID 845544Notes

Reaction equation

HRID 845544 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:14])[C:5]2[C:10]([C:11](=[O:13])[CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H][H]>O1CCCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][C:3](=[O:2])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[O:14][C:11](=[O:13])[CH3:10]

Participants

5

Reactant 2

HCID 168712-Methoxy-1,4-NaphthoquinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 6052732-Methoxy-1,4-diacetyloxynaphthalene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the calculated amount of hydrogen was absorbed, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour the catalyst was filtered off and the solvent removed from the filtrate under reduced pressure. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2-methoxy-1,4-diacetyloxynaphthalene, m.p. 135°-136° C.

Workup

  1. customwas absorbed, approximately 4 hours
  2. additionWhile still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture
  3. filtrationwas filtered off
  4. customthe solvent removed from the filtrate under reduced pressure
  5. dissolutionThe residue was dissolved in ether (100 mL)
  6. washwas washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customRecrystallization from ether

Sources & evidence

ORD record
ord-311bff6d546b4a22b66698e1a70d8775
Source dataset
uspto-grants-1988_07
Patent number
US04758587

Reaction notes

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