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 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).

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

ORD record

ord-3cf02b5c4a2747698f7d74e8938944ae

Source dataset

uspto-grants-1988_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04737590