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

HRID 845543

Reaction equation

HRID 845543 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-111067d78c4e48748110f7d3c7226caa
Source dataset
uspto-grants-1988_07
Patent number
US04758587

Linked notes

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