Reaction #465967

Reaction equation

methyl 3,4,6-Trichloropicolinate

NaOH

→

white solid

Yield 93.1%

3,4,6-Trichloropyridine-2-carboxylic Acid

Yield 93.1%

Solvents

methanol

Conditions

Workup

1. 1
   Concentrationconcentrated to dryness in vacuo
2. 2
   workup.ADDITION100 mL each of diethyl ether and H2O were added
3. 3
   workup.ADDITIONMethylene chloride was added
4. 4
   Extractionthe aqueous phase was extracted with additional CH2Cl2 (2×100 mL)
5. 5
   DryingThe combined extracts were dried (MgSO4)
6. 6
   Concentrationconcentrated

Procedure

To methyl 3,4,6-Trichloropicolinate (3.57 g, 14.85 mmol) in 20 mL of methanol was added 1N NaOH (14.85 mL, 14.85 mmol). The reaction mixture was stirred at room temperature for 1 hr and then concentrated to dryness in vacuo. 100 mL each of diethyl ether and H2O were added. Aqueous layer was acidified with 1N HCl until pH=2. Methylene chloride was added and the aqueous phase was extracted with additional CH2Cl2 (2×100 mL). The combined extracts were dried (MgSO4) and concentrated to give 3.13 g of a white solid. 1H NMR(CDCl3): δ 7.50 (s, 1H).

Source