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

HRID 2232119Notes

Reaction equation

HRID 2232119 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.[CH3:14][O-:15].[Na+]>O1CCCC1>[CH3:14][O:15][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 10942334Sodium Methoxide

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 methoxide (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-b4541e659bf844e7a5365aae2ae46aae
Source dataset
uspto-grants-1988_11
Patent number
US04786652

Reaction notes

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