Sodium Hydroxide → (1-Chlorocycloheptyl)phenylmethanone

Participants

Reaction Conditions

Reaction Steps

Sulfuryl chloride (210 mL) was added dropwise to neat cycloheptyl-phenyl-methanone (Example 14a) (86.5 g) at 0° C. over approximately 1 hour. Gas evolution and an exotherm were observed. The internal temperature was kept below 15° C. during the addition and the evolved gas was scrubbed by passing through a 10.2M aqueous solution of NaOH. The reaction mixture was heated to reflux overnight. The reaction mixture was cooled to 0° C and poured slowly onto ice (1 L) with stirring. The layers were separated and the aqueous layer was extracted with ether (2×400 mL). The combined organic layers were washed with water (600 mL), saturated aqueous sodium hydrogen carbonate (600 mL), and brine (600 mL), dried over magnesium sulphate, filtered and evaporate to give the sub-titled compound as a brown oil (100 g).

Provenance & Evidence