Water → 1-Chloro-5-hydroxy-5-methyl-6-heptyne

200 g (2.17 mol) of lithium acetylide in the form of the ethylenediamine complex were suspended in 800 ml of dry dioxane and, while stirring vigorously and cooling in ice, 269.2 g (2.0 mol) of 1-chloro-5-hexanone were rapidly added dropwise, during which the temperature rose to 48° C. The exothermic reaction was allowed to subside while stirring for 3 hours without further external cooling, 500 ml of water were cautiously added, the mixture was filtered, most of the dioxane was distilled off under reduced pressure, the aqueous phase was extracted exhaustively with chloroform, the extract was dried over sodium sulfate, the solvent was evaporated off under reduced pressure, and the residue was subjected to fractional distillation.

1. temperaturecooling in ice
2. customrose to 48° C
3. customThe exothermic reaction
4. additionwere cautiously added
5. filtrationthe mixture was filtered, most of the dioxane
6. distillationwas distilled off under reduced pressure
7. extractionthe aqueous phase was extracted exhaustively with chloroform
8. dry with materialthe extract was dried over sodium sulfate
9. customthe solvent was evaporated off under reduced pressure
10. distillationthe residue was subjected to fractional distillation

ORD record

ord-645b846b761c4cf7a9c407285bf7c9ca

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05965555