Methanol → 1-Hydroxy-2,4-dimethoxynaphthalene

HRID 466212Notes

Reaction equation

HRID 466212 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.S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:23]O>>[OH:14][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]([O:13][CH3:23])=[CH:12][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 168712-Methoxy-1,4-NaphthoquinoneHCID 24489Sodium Dithionite

Product 1

HCID 125635471-Hydroxy-2,4-dimethoxynaphthalene

Procedure

A solution of 18.9 g of 2-methoxynaphthoquinone in methanol was added slowly to a solution of 34.8 g of sodium hydrosulfite in methanol and the mixture stirred for 1 hour. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate and evaporated to a purple solid. The solid was dissolved in 200 ml of methanol previously saturated with anhydrous hydrochloric acid and stirred for 3 minutes at 60° C. The mixture was then diluted with 200 ml of ice water and the precipitate filtered off, dried under vacuum and recrystallized from ether/pentane to give 13.25 g of 1-hydroxy-2,4-dimethoxynaphthalene, m.p. 87°-88° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated to a purple solid
  5. dissolutionThe solid was dissolved in 200 ml of methanol previously saturated with anhydrous hydrochloric acid
  6. stirringstirred for 3 minutes at 60° C
  7. additionThe mixture was then diluted with 200 ml of ice water
  8. filtrationthe precipitate filtered off
  9. customdried under vacuum
  10. customrecrystallized from ether/pentane

Sources & evidence

ORD record
ord-16e4cbd5795d4f0e898cf49154d074ef
Source dataset
uspto-grants-1992_10
Patent number
US05155132

Reaction notes

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