Reaktion #631989

Reaktionsgleichung

α-damascone

N,N-dimethylaminoethanol

tetramethylguanidine

→

product

Ausbeute 32.0%

3-[2-(dimethylamino)ethoxy]-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone

Ausbeute 32.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONAfterward, the excess of N,N-dimethylaminoethanol was distilled at ca. 60° C./10 to 2 mbar
2. 2
   workup.ADDITIONThe crude product was diluted in diethyl ether (Et2O)
3. 3
   Extraktionthis mixture was extracted with 5% aqueous HCl
4. 4
   Waschenwashed with water and saturated aqueous NaCl
5. 5
   Extraktionextracted twice with ether
6. 6
   Sonstigeto recover the crude product in the organic phases
7. 7
   WaschenThe organic phases were still washed with water and brine
8. 8
   Trocknendried over Na2SO4
9. 9
   Einengenconcentrated
10. 10
    workup.DISTILLATIONBulb-to-bulb distillation of the crude product (100-125° C./0.05 mbar)

Vorschrift

A solution of α-damascone (6.44 g; 33.5 mmol), N,N-dimethylaminoethanol (30.25 ml; 301 mmol) and tetramethylguanidine (TMG) (0.77 g; 6.70 mmol) was heated at 70° C. for 15 h. Afterward, the excess of N,N-dimethylaminoethanol was distilled at ca. 60° C./10 to 2 mbar. The crude product was diluted in diethyl ether (Et2O) and this mixture was extracted with 5% aqueous HCl and washed with water and saturated aqueous NaCl. The combined aqueous phases were basified using aqueous NaOH and extracted twice with ether to recover the crude product in the organic phases. The organic phases were still washed with water and brine, then dried over Na2SO4 and concentrated. Bulb-to-bulb distillation of the crude product (100-125° C./0.05 mbar) afforded 2.94 g of the desired pure product (yield: 32%).

Quelle