Reacción #54508

Ecuación de reacción

sodium hydroxide

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

sulfuric acid

→

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

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISSOLUTIONto dissolve the organic matter and air
2. 2
   Otrowas then bubbled through the solution for 3 hours
3. 3
   ExtracciónThe resulting solution was extracted with 100 parts petroleum ether (twice),
4. 4
   Extracciónre-extracted with diethylether
5. 5
   ExtracciónThe ether extract
6. 6
   Lavadowas washed with saturated sodium chloride
7. 7
   Secadodried over magnesium sulfate
8. 8
   Otroevaporated
9. 9
   Filtraciónfiltered
10. 10
    OtroThe filtrate was evaporated to dryness
11. 11
    Otrothe residue triturated with petroleum ether

Procedimiento

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.

Fuente