Hydrochloric Acid → 3-Methoxyoct-1-yne

Temperature

60 °C

To an ice-cooled solution of 63 g. of 1-octyne-3-ol in 300 ml. of dimethoxyethane is added under an inert atmosphere 312 ml. of 1.6 M n-butyllithium in hexane dropwise over 1 hour. To the mixture is then added 145 g. of methyl iodide and the resulting mixture is stirred at ambient temperatures for 24 hours and then heated to 60° C. for 1 hour. The mixture is cooled and poured into cold dilute hydrochloric acid. The organic phase is separated, washed with water and saturated brine, dried (Na2SO4), and evaporated to an oil, dried (Na2SO4), and evaporated to an oil. Fractional distillation of the oil in vacuo yields the product as a colorless oil.

1. additionTo the mixture is then added 145 g
2. temperatureThe mixture is cooled
3. customThe organic phase is separated
4. washwashed with water and saturated brine
5. dry with materialdried (Na2SO4)
6. customevaporated to an oil
7. dry with materialdried (Na2SO4)
8. customevaporated to an oil
9. distillationFractional distillation of the oil in vacuo

ORD record

ord-4799ce471ff6456e8f8fa0347df48616

Source dataset

uspto-grants-1980_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04236027