Propargyl bromide → HCID 12786185, compound

To a stirred suspension of 2.1 g. of magnesium and 20 mg. of mercuric chloride in 25 ml. of ether is added 0.8 ml. of propargyl bromide. After a few minutes of vigorous stirring, to this is added a mixture of 10.75 g. of 1-chloro-2-hexanone and 7.2 ml. of propargyl bromide in 25 ml. of ether, at such a rate that the reaction mixture is maintained at 25°-28° C. After addition, the mixture is stirred at room temperature one hour, cooled in an ice-water bath and 30 ml. of saturated ammonium chloride is added dropwise. The mixture is filtered through celite and washed with ether. The ether solution is concentrated to give 11.0 g. of a yellow liquid which is vacuum distilled to give 6.9 g. of product as a colorless liquid at b.p. 60°-61° C./-4 mm.; PMRδ 3.62 (ABq, CH2Cl), 2.53 (d, J=3,C≡C--CH2), 2.06 (t, j=3, HC≡C).

1. additionTo a stirred suspension of 2.1 g
2. waitAfter a few minutes of vigorous stirring
3. additionto this is added
4. additiona mixture of 10.75 g
5. additionAfter addition
6. temperaturecooled in an ice-water bath
7. filtrationThe mixture is filtered through celite
8. washwashed with ether
9. concentrationThe ether solution is concentrated
10. customto give 11.0 g
11. distillationdistilled
12. customto give 6.9 g

ORD record

ord-3af6831ceab54c2e86d113cdbeb3f24b

Source dataset

uspto-grants-1981_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04297516