Epichlorohydrin → HCID 13038067, compound

Participants

Reaction Steps

To a hot (130° C.) solution of 105 g (0.64 mole) of 4-methylthiophenyl isocyanate and 93 g (1 mole) of epichlorohydrin in 600 ml of xylene was added 200 ml of tri-n-butylphosphine oxide-lithium bromide complex. (The complex was prepared by heating a mixture of 45 g of tri-n-butylphosphine oxide, 12.7 g of lithium bromide and 550 ml of xylene to reflux until a clear solution was obtained by removing water.) An exothermic reaction took place. After all of the catalyst had been added, the mixture was heated under reflux for 1 hour and cooled. The solution was decanted into a flask and concentrated to one-half the volume. An equal volume of petroleum ether was added to the residue. The solid that formed was collected by filtration and recrystallized from acetonitrile to give 102 g (62% yield) of the title compound; m.p. 106.5°-107.5° C.

Provenance & Evidence