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

A mixture of 300 g. of aluminum bromide and 250 ml. of 1,2-dibromoethane, cooled in an ice bath and protected from moisture, is saturated with acetylene. To the mixture is added with ice cooling 150 g. of hexanoyl bromide (Example 991) over a period of 20 minutes and the resulting mixture is treated with acetylene until gas uptake ceases. The reaction mixture is poured onto 500 ml. of saturated brine and 500 g. of ice. The resulting mixture is extracted twice with 500 ml. of ether. The combined organic extracts are washed twice with 500 ml. of saturated brine and dried with anhydrous sodium sulfate. To the organic phase is added 5 g. of hydroquinone and the solvent is evaporated in vacuo to yield the crude 1-bromo-trans-1-octen-3-one.

1. additionA mixture of 300 g
2. additionThe reaction mixture is poured onto 500 ml
3. extractionThe resulting mixture is extracted twice with 500 ml
4. washThe combined organic extracts are washed twice with 500 ml
5. dry with materialof saturated brine and dried with anhydrous sodium sulfate
6. additionTo the organic phase is added 5 g
7. customof hydroquinone and the solvent is evaporated in vacuo

ORD record

ord-bf7c3554dc014fa186cde9e2f3f2c068

Source dataset

uspto-grants-1978_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04123456