Hydrochloric Acid → 2,4-Dimethyl-3-cyclohexene carboxaldehyde

HRID 224240

Reaktionsgleichung

Reaktionsgleichung von HRID 224240
Cl[CH:2]([CH3:4])[CH3:3].[Mg:5].[CH3:6][CH:7]1[CH:12]=[C:11]([CH3:13])[CH2:10][CH2:9][CH:8]1[CH:14]=[O:15].[ClH:16]>CCOCC>[CH:2]([Mg:5][Cl:16])([CH3:4])[CH3:3].[CH3:6][CH:7]1[CH:12]=[C:11]([CH3:13])[CH2:10][CH2:9][CH:8]1[CH:14]=[O:15]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 63612-ChloropropaneHCID 933752,4-Dimethyl-3-cyclohexene carboxaldehydeHCID 5462224Magnesium

Produkt 2

HCID 933752,4-Dimethyl-3-cyclohexene carboxaldehydeHCID 178418918HCID 178418918, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel4×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of isopropyl magnesium chloride in ether is prepared by dropwise adding a solution of 164 grams (2.1 moles) of 2-chloropropane in 200 ml of ether to a stirred slurry of 50 grams (2.1 moles) of magnesium in 500 ml of ether at reflux under nitrogen. The resulting solution is stirred at reflux for 30 minutes. A solution of 164 grams (2 moles) of 2,4-dimethyl-3-cyclohexene-carboxaldehyde in 200 ml of ether is added over a 45-minute period to the reaction mixture at reflux under nitrogen. The resulting slurry is heated at reflux for 30 minutes and then cooled to 0° C. 400 ml of 18% aqueous hydrochloric acid is slowly added with cooling and stirring. Two clear layers are formed. The aqueous layer is discarded and the organic layer is washed twice with H2O, neutralizing the second wash with aqueous caustic soda. The ether is removed by distillation at atmospheric pressure. Fractional distillation of the remaining oil (375 grams) through a 11/2"×12" Goodloe packed column affords 121 grams of recovered 2,4-dimethyl-3-cyclo-hexenecarboxaldehyde; 54 grams of 1,5-dimethyl-3-isopropyl-2-oxabicyclo[2.2.2]octane; and 173 grams of 2,4-dimethyl-alpha-isopropyl-3-cyclohexene-1-methanol (b.p. 91° C., 2.1 mm Hg pressure).

Aufarbeitung

  1. temperatureat reflux under nitrogen
  2. temperatureat reflux for 30 minutes
  3. temperatureat reflux under nitrogen
  4. temperatureThe resulting slurry is heated
  5. temperatureat reflux for 30 minutes
  6. temperaturewith cooling
  7. stirringstirring
  8. customTwo clear layers are formed
  9. washthe organic layer is washed twice with H2O
  10. washsecond wash with aqueous caustic soda
  11. customThe ether is removed by distillation at atmospheric pressure
  12. distillationFractional distillation of the remaining oil (375 grams) through a 11/2"×12" Goodloe

Quellen und Nachweise

ORD-Eintrag
ord-52969ef372ed446b9a92dcbebbce3744
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04231940

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