Caprolactam → 2H-Azepin-2-one, hexahydro-N-lauroyl-

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Reaction Steps

Sodium hydride [5.14 g (50% oil dispersion); 0.107 mol] in 100ml of dry toluene was added to a 500 ml, 3-necked flask fitted with a mechanical stirrer. Azacycloheptan-2-one (10.07 g; 0.089 mol) was dissolved in 50ml of dry toluene with slight warming and added to the sodium hydride suspension dropwise at room temperature. The suspension was stirred at room temperature for 1 hour. n-Dodecanoyl chloride (19.39 g; 0.089 mol) in 10ml of dry toluene was added dropwise to the mixture and after the addition was complete, the mixture was stirred overnight at room temperature. The mixture was then washed with water, and the organic layer separated, dried with MgSO4, and concentrated. The resulting yellow oil was distilled 160° C./0.35mm to yield 1-n-dodecanoylazacycloheptan-2-one as clear oil.

Provenance & Evidence