Reacción #95275

Ecuación de reacción

acetylene

aluminum chloride

hexanoyl chloride

→

1-chloro-trans-1-octen-3-one

Disolventes

carbon tetrachloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis added over 20 minutes 201.9 g
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Otroacetylene is bubbled into the mixture as rapidly as it
4. 4
   Otrois absorbed and for 1 hour
5. 5
   Otroafter absorption
6. 6
   workup.ADDITIONThe mixture is poured onto 1700 g
7. 7
   OtroThe organic phase is separated
8. 8
   Lavadothe aqueous phase is washed with ether
9. 9
   LavadoThe combined organic phase and washings are washed with saturated brine
10. 10
    Secadodried (Na2SO4)
11. 11
    Otroevaporated
12. 12
    workup.DISTILLATIONof hydroquinone and distilled
13. 13
    Otroto yield a colorless oil, b.p. 51°-52° C. (0.10 torr)

Procedimiento

To a slurry of 233.5 g. (1.75 moles) of aluminum chloride in 390 ml. of carbon tetrachloride, saturated with acetylene and cooled in an ice bath, is added over 20 minutes 201.9 g. (1.50 moles) of hexanoyl chloride. After the addition is complete, acetylene is bubbled into the mixture as rapidly as it is absorbed and for 1 hour after absorption becomes slow. The mixture is poured onto 1700 g. of ice and 720 ml. of saturated brine. The organic phase is separated and the aqueous phase is washed with ether. The combined organic phase and washings are washed with saturated brine, dried (Na2SO4) and evaporated. The residual oil is combined with 10 g. of hydroquinone and distilled to yield a colorless oil, b.p. 51°-52° C. (0.10 torr).

Fuente