Toluene → HCID 2387345, compound

Participants

Reaction Steps

A sample of 5.9 grams (0.105 mole) of potassium hydroxide was ground to a powder and placed in the reaction vessel. To this was added 270 ml of dry toluene, followed by 20.0 grams (0.105 mole) of 2,6-dichlorobenzoic acid. The stirred reaction mixture was heated under reflux while the water by-product was collected by azeotropic distillation using a Dean-Stark trap. A total of 2.8 ml of water was collected during a 30-minute period. At the end of this time the reaction mixture was cooled slightly and 2.0 grams of 1,4,7,10,13,16-hexaoxacyclooctadecane, followed by 9.8 grams (0.105 mole) of chloroacetamide were added. Upon completion of the addition the reaction mixture was heated under reflux for 18 hours. the reaction mixture was cooled to ambient temperature and the toluene layer was separated from the two-phase system and washed with one portion of 100 ml of water. An emulsion formed but was broken up by the addition of 100 ml of ethyl acetate. The organic layer was separated and dried with sodium sulfate. The mixture was filtered, and the filtrate evaporated under reduced pressure to a residual semi-solid. The solid was recrystallized twice from high-boiling petroleum ether-ethyl acetate using decolorizing carbon to give 12.6 grams of (aminocarbonyl)methyl 2,6-dichlorobenzoate; mp 113.5°-115.5°. The ir and the nmr spectra were consistent with the proposed structure.

Provenance & Evidence