Reaktion #54508

Reaktionsgleichung

sodium hydroxide

ethyl 2-[(2-methylphenyl)acetyl]tetradecanoate

sulfuric acid

→

2-dodecyl-3-hydroxy-5-methyl-1,4-napthoquinone

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONto dissolve the organic matter and air
2. 2
   Sonstigewas then bubbled through the solution for 3 hours
3. 3
   ExtraktionThe resulting solution was extracted with 100 parts petroleum ether (twice),
4. 4
   Extraktionre-extracted with diethylether
5. 5
   ExtraktionThe ether extract
6. 6
   Waschenwas washed with saturated sodium chloride
7. 7
   Trocknendried over magnesium sulfate
8. 8
   Sonstigeevaporated
9. 9
   Filtrationfiltered
10. 10
    SonstigeThe filtrate was evaporated to dryness
11. 11
    Sonstigethe residue triturated with petroleum ether

Vorschrift

Four parts of crude ethyl 2-[(2-methylphenyl)acetyl]tetradecanoate obtained in Example 3 was combined with 12 parts of cold concentrated sulfuric acid and stirred at room temperature for 66 hours. The mixture was poured into ice water and made slightly basic by the addition of 50% aqueous sodium hydroxide. Enough ethanol was added to dissolve the organic matter and air was then bubbled through the solution for 3 hours. The resulting solution was extracted with 100 parts petroleum ether (twice), acidified with hydrochloric acid and re-extracted with diethylether. The ether extract was washed with saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue was taken up in acetonitrile and filtered. The filtrate was evaporated to dryness and the residue triturated with petroleum ether to give 0.2 g of 2-dodecyl-3-hydroxy-5-methyl-1,4-napthoquinone, m.p. 92°-93° C.

Quelle