Thionyl Chloride → Laurolactam

Participants

Reaction Conditions

Reaction Steps

Within a glove box, 0.033 g (0.17 mmol) of cyclododecanone oxime prepared in Reference Example 2 was dissolved in 0.400 g of a 5% by weight thionyl chloride (rearrangement catalyst)/toluene solution (0.020 g (0.17 mmol) as pure thionyl chloride), and the mixture was stirred using a magnetic stirrer at room temperature (25° C.) for 5 min, to conduct the pre-preparation of a rearrangement catalyst. After the pre-preparation, high performance liquid chromatography analysis indicated that cyclododecanone oxime had been consumed. Separately, within a glove box (under nitrogen atmosphere), in a flat-bottom flask equipped with a manifold, 3.285 g (16.64 mmol) of cyclododecanone oxime and 0.023 g (0.17 mmol) of zinc chloride were weighed and then 7.00 g of toluene was added, and the materials were dissolved by heating the mixture to 100° C. in an oil bath. To the zinc-chloride containing solution of cyclododecanone oxime in toluene, the reaction mixture which had been prepared in the pre-preparation using cyclododecanone oxime and thionyl chloride in 1:1 molar ratio was added, which then reacted for 60 min. The reaction solution was clear without turbidity, and gas chromatography analysis indicated that a conversion of cyclododecanone oxime was 100% and a laurolactam yield was 98.8%.

Provenance & Evidence