Potassium Hydroxide → HCID 12832595, compound

Participants

Reaction Steps

Potassium hydroxide, 0.8 gram (0.012 mole), was powdered and dissolved in 50 ml of ethanol. The solution was warmed to 40°-50° and 3.1 grams (0.011 mole) of (ethoxycarbonyl)methyl 2,6-dichlorobenzoate (the compound of Example IX) was added in portions during a 5-minute period. Upon completion of the addition a precipitate formed. The reaction mixture was stirred at ambient temperature for 18 hours. The potassium salt was collected by filtration, washed with ethanol, dried, placed in an Erlenmeyer flask, and stirred with 50 ml of water. To the resultant solution was added a solution of 10 ml of concentrated hydrochloric acid in 40 ml of water. The solid precipitate was collected by filtration and washed with water. The filter cake was dissolved in 100 ml of ethyl acetate and dried with sodium sulfate. The mixture was filtered and the filtrate evaporated under reduced pressure to give 1.1 grams of carboxymethyl 2,6-dichlorobenzoate; mp 180°-181.5°. The nmr and the ir spectra were consistent with the proposed structure.

Provenance & Evidence