Benzenesulfonyl chloride → 5-Undecanone

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3 grams (18 mmol) of 2-adamantanone oxime in 36 ml of 20% aqueous sodium hydroxide were added 5 grams (28 mmol) of benzenesulfonyl chloride with vigorous stirring at a temperature of 20°-30° C. The temperature was maintained below 30° C. until the exothermic reaction ceased, then raised to 55° C. and held there for 2 hours. The reaction mixture was worked up leaving 2 grams of 4-azatricyclo[4.3.1.13,8 ]undecan-5-one as white crystals melting at 306°-308° C. (recrystallized from hexane).

Provenance & Evidence