Potassium Hydroxide → Clomazone

Participants

Reaction Steps

To a stirred solution of 6.3 grams (0.023 mole) of 3-chloro-N-(2-chlorophenyl)methyl-N-hydroxy-2,2-dimethylpropanamide (prepared in Example 1) in 45 ml of methanol was added dropwise a solution of 1.5 grams (0.023 mole) potassium hydroxide (85% pure) in 25 ml of methanol. The addition required 15 minutes during which time the reaction mixture temperature rose from 24° to 32°. Upon completion of addition the reaction mixture was stirred for 18 hours at ambient temperature. The reaction mixture was filtered to remove by-product potassium chloride. The filtrate was poured into 500 ml of ice-water. The mixture was extracted with two portions of 250 ml each of methylene chloride. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 5.2 grams of 2-(2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone as an oil.

Provenance & Evidence