Sulfuric Acid → HCID 178442825, Verbindung

HRID 1834532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1834532
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:12]([O:14]CC)=O)=[O:10].S(=O)(=O)(O)[OH:30].[OH-].[Na+]>C(O)C>[CH2:17]([C:11]1[C:12](=[O:14])[C:4]2[C:3]([C:8](=[O:30])[C:9]=1[OH:10])=[C:2]([CH3:1])[CH:7]=[CH:6][CH:5]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21325239Ethyl 2-[(2-methylphenyl)acetyl]tetradecanoate

Produkt 1

HCID 178442825HCID 178442825, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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-naphthoquinone, m.p. 92°-93° C.

Aufarbeitung

  1. dissolutionto dissolve the organic matter and air
  2. customwas then bubbled through the solution for 3 hours
  3. extractionThe resulting solution was extracted with 100 parts petroleum ether (twice),
  4. extractionre-extracted with diethylether
  5. extractionThe ether extract
  6. washwas washed with saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness
  11. customthe residue triturated with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-4c58eecd121146d8855403d64195253b
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04070481

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