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ChemicalBook CAS DataBase List 4-TERT-BUTYLPICOLINIC ACID
42205-74-3

4-TERT-BUTYLPICOLINIC ACID synthesis

3synthesis methods
-

Yield:42205-74-3 68.4%

Reaction Conditions:

with sodium nitrite in ice-water;hexane;sulfuric acid;water;

Steps:

4.3 II-4-3:

II-4-3: Synthesis of 4-t-butylpicolinic acid A solution of 1.70 g (11 mmol) of 2-cyano-4-t-butylpyridine dissolved in 15 g of 90% sulfuric acid was stirred ar 115° to 125° C. for 2 hours, then a solution of 3.00 g of sodium nitrite in 6 ml of water was added dropwise at 20° to 25° C., and stirred at the same temperature for 1.5 hours, and further, under heating at 70° to 80° C. for 1.5 hours. After cooling, 50 g of ice-water was added, and the mixture was adjusted to a pH of about 2, with sodium carbonate. The mixture was extracted with dichloromethane, dried over anhydrous sodium sulfate, and then concentrated under a reduced pressure. The residue was solidified by an addition of hexane, and the solid was collected by filtration. Recrystallization from a hexane-isopropyl ether mixture gave 1.30 g of colorless crystals (yield 68.4%). m.p.: 134°-135° C. IR (KBr): 1720, 1600 cm-1.

References:

US5219847,1993,A

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