Methanol → 1-Hydroxy-2,4-dimethoxynaphthalene
Reaktionsgleichung
[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]Komponenten
4
Versuchsvorschrift
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.
Aufarbeitung
- customThe solvent was removed under reduced pressure
- customthe residue partitioned between ethyl acetate and water
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customevaporated to a purple solid
- dissolutionThe solid was dissolved in 200 ml of methanol previously saturated with anhydrous hydrochloric acid
- stirringstirred for 3 minutes at 60° C
- additionThe mixture was then diluted with 200 ml of ice water
- filtrationthe precipitate filtered off
- customdried under vacuum
- customrecrystallized from ether/pentane
Quellen und Nachweise
- ORD-Eintrag
- ord-36eeac991cca4015885d5799699d49fa
- Quelldatensatz
- uspto-grants-1988_07
- Patentnummer
- US04758587
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