Acetylene → HCID 13434207, compound

A solution of 200 ml of octanoyl chloride (A6R1 =C2H5) in 750 ml of carbon tetrachloride is cooled on an ice bath and treated with 214 g of aluminum chloride in three portions over a 1 hour period while acetylene is bubbled through the solution. The ice bath is removed and the reaction mixture stirred at room temperature for 3 hours with additional acetylene being added. At the end of this period, the reaction mixture is poured into 4 kg of ice. The organic layer is separated and the aqueous layer extracted twice with 500 ml of chloroform. The combined organic extracts are washed once with 500 ml of water, dried over anhydrous sodium sulfate and concentrated in vacuo. Distillation of the residue yields 142 g of trans-1-chloro-dec-1-en-3-one, (A5R1 =C2H5).

1. customis bubbled through the solution
2. customThe ice bath is removed
3. additionadded
4. additionAt the end of this period, the reaction mixture is poured into 4 kg of ice
5. customThe organic layer is separated
6. extractionthe aqueous layer extracted twice with 500 ml of chloroform
7. washThe combined organic extracts are washed once with 500 ml of water
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated in vacuo
10. distillationDistillation of the residue

ORD record

ord-101dee49e0834b2dae72c097d3c7fa31

Source dataset

uspto-grants-1979_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04164446