Reacción #631989

Ecuación de reacción

α-damascone

N,N-dimethylaminoethanol

tetramethylguanidine

→

product

Rendimiento 32.0%

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

Rendimiento 32.0%

Condiciones de reacción

Tratamiento posterior

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
   Extracciónthis mixture was extracted with 5% aqueous HCl
4. 4
   Lavadowashed with water and saturated aqueous NaCl
5. 5
   Extracciónextracted twice with ether
6. 6
   Otroto recover the crude product in the organic phases
7. 7
   LavadoThe organic phases were still washed with water and brine
8. 8
   Secadodried over Na2SO4
9. 9
   Concentraciónconcentrated
10. 10
    workup.DISTILLATIONBulb-to-bulb distillation of the crude product (100-125° C./0.05 mbar)

Procedimiento

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%).

Fuente