Chloroacetic Acid → HCID 57240918, compound

Participants

Reaction Steps

Monochloroacetic acid (8.5 g.) in water (10 ml.) was neutralised with sodium hydroxide (3.6 g.) in water (10 ml.). 1,2,5,6-Tetrahydropyridine (7.57 g.) was added. An exothermic reaction set in and after 30 minutes the pH of he dark red solution had changed from 9 to 8. After 24 hours the reaction mixture was evaporated, the residue was triturated with absolute ethanol ( 100 ml.) and filtered. The filtrate was evaporated, barium hydroxide (14 g.) in water (40 ml.) was added to the residue and evaporated repeatedly from water. The residue was redissolved in hot water, treated with CO2 gas, and filtered. The filtrate was evaporated to dryness and the residue, dissolved in hot absolute ethanol, (100 ml.) was acidified to pH 3-4 (2N H2SO4) and centrifuged to remove inorganic material. The supernatant liquor was evaporated to give 1,2,5,6-tetrahydropyridinyl acetic acid (11.1 g.) as an intractable dark brown gum.

Provenance & Evidence