Acetylene → 1-Chloro-trans-1-octen-3-one

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 addtion 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 satuated 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).

1. additionis added over 20 minutes 201.9 g
2. customacetylene is bubbled into the mixture as rapidly as it
3. customis absorbed and for 1 hour
4. customafter absorption
5. additionThe mixture is poured onto 1700 g
6. customThe organic phase is separated
7. washthe aqueous phase is washed with ether
8. washThe combined organic phase and washings are washed with satuated brine
9. dry with materialdried (Na2SO4)
10. customevaporated
11. distillationof hydroquinone and distilled
12. customto yield a colorless oil, b.p. 51°-52° C. (0.10 torr)

ORD record

ord-cf8e0b810568455ba668be0775e8e56e

Source dataset

uspto-grants-1984_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04439365