2-Chloro-1,4-naphthoquinone → 2-Methoxy-1,4-Naphthoquinone

HRID 1534703Notes

Reaction equation

HRID 1534703 reaction equation
Cl[C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[O-:14][CH2:15]C.[Na+]>O1CCCC1>[CH3:15][O:14][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 138912-Chloro-1,4-naphthoquinoneHCID 2723922Sodium ethoxide

Product 1

HCID 168712-Methoxy-1,4-Naphthoquinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-chloro-1,4-naphthoquinone (10.3 g) in tetrahydrofuran (100 mL) was treated with a suspension of sodium ethoxide (3.20 g) in tetrahydrofuran (25 mL) at room temperature. After stirring overnight, the mixture was evaporated, and the residue was taken up in ether. The organic layer was washed with brine, dried, filtered and evaporated. Chromatography over silica gel gave 2-methoxy-1,4-naphthoquinone, m.p. 182°-183° C.

Workup

  1. customthe mixture was evaporated
  2. washThe organic layer was washed with brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-8dfb5281c2c2455e805c5f2599de9f4a
Source dataset
uspto-grants-1992_02
Patent number
US05089657

Reaction notes

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