Chloroacetic Acid → HCID 57240918, compound

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.

1. customAn exothermic reaction
2. customafter 30 minutes
3. customAfter 24 hours the reaction mixture was evaporated
4. customthe residue was triturated with absolute ethanol ( 100 ml.)
5. filtrationfiltered
6. customThe filtrate was evaporated
7. additionbarium hydroxide (14 g.) in water (40 ml.) was added to the residue
8. customevaporated repeatedly from water
9. dissolutionThe residue was redissolved in hot water
10. additiontreated with CO2 gas
11. filtrationfiltered
12. customThe filtrate was evaporated to dryness
13. dissolutionthe residue, dissolved in hot absolute ethanol
14. customcentrifuged to remove inorganic material
15. customThe supernatant liquor was evaporated

ORD record

ord-e0425cf922df4db5b734b0d5c25c260d

Source dataset

uspto-grants-1976_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03959260