Nitric Acid → 3'-Nitrobutyrophenone

HRID 1826452

Reaktionsgleichung

Reaktionsgleichung von HRID 1826452
[N+:1]([O-:4])(O)=[O:2].[C:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])[CH2:6][CH2:7][CH3:8].[N+]([O-])(O)=O.S(=O)(=O)(O)O>S(=O)(=O)(O)O>[N+:1]([C:12]1[CH:11]=[C:10]([C:5](=[O:9])[CH2:6][CH2:7][CH3:8])[CH:15]=[CH:14][CH:13]=1)([O-:4])=[O:2]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 10315ButyrophenoneHCID 71777668Sulfuric acid, mixt. with nitric acid

Produkt 1

HCID 1427473'-NitrobutyrophenoneAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel3×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

Concentrated nitric acid (40 ml) was added cautiously with cooling to concentrated sulphuric acid (100 ml) maintaining a temperature of −5° C. Another solution of butyrophenone (59.2 g, 0.47 mol) in concentrated sulphuric acid (140 ml) was made up with shaking, keeping the temperature at −5° C. (+/−5° C.). The former nitric acid/sulphuric acid solution was added portionwise over 45 min to the latter solution of ketone in sulphuric acid keeping the temperature at −10° C.(+/−5° C. during the addition and for a subsequent 30 min. The reaction mixture was poured onto crushed ice (1.5 l) and then extracted with diethyl ether (200 ml and then 3×100 ml). The combined organic extracts were washed with water and then aqueous saturated sodium hydrogen carbonate solution and dried (MgSO4) before concentrating in vacuo. The crude yellow oil crystallised after 16 h and was then purified by chromatography on silica gel (1 kg) eluting with hexane:diethyl ether (9:1) to give the title compound as a white solid (9.1 g, 10%).

Aufarbeitung

  1. customat −5° C.
  2. custom(+/−5° C.)
  3. additionduring the addition
  4. additionThe reaction mixture was poured
  5. extractionextracted with diethyl ether (200 ml
  6. washThe combined organic extracts were washed with water
  7. dry with materialaqueous saturated sodium hydrogen carbonate solution and dried (MgSO4)
  8. concentrationbefore concentrating in vacuo
  9. customThe crude yellow oil crystallised after 16 h
  10. customwas then purified by chromatography on silica gel (1 kg)
  11. washeluting with hexane:diethyl ether (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-13469da1c5d34533ac792ed1aaee33bc
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049444B2

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