Potassium Hydroxide → HCID 86709870, compound

HRID 541048Notes

Reaction equation

HRID 541048 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:17]([O:19]C(C)C)=[O:18])[CH:3]=1.[OH-].[K+]>O1CCCC1.O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[N:5]=[C:4]([C:17]([OH:19])=[O:18])[CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86709871HCID 86709871, compound

Product 1

HCID 86709870HCID 86709870, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of isopropyl 4,5-dichloro-6-(4-methoxyphenyl)picolinate (5.25 g, 15.4 mmol) in tetrahydrofuran (40 mL) and water (10 mL) was added potassium hydroxide (1.26 g, 22.4 mmol). The reaction mixture was allowed to stir at room temperature for 12 h. After 1 hour of stirring, solids precipitated from the mixture. HCl (aq) (2N, 25 mL) was added to the reaction mixture, and it formed a clear biphasic mixture. The mixture was added to water (75 mL) in a reparatory funnel and extracted with EtOAc (2×75 mL). The combined organic layers were washed with water (25 mL) and saturated NaCl (50 mL) and then concentrated under reduced pressure to provide 4.57 g (99% yield) of 4,5-dichloro-6-(4-methoxyphenyl)picolinic acid as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.72-7.64 (m, 2H), 7.07-6.99 (m, 2H), 3.89 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 162.78, 161.05, 157.26, 146.30, 143.76, 133.54, 130.98, 128.72, 123.45, 113.77, 55.48; mp=164-181° C.

Workup

  1. stirringAfter 1 hour of stirring
  2. customsolids precipitated from the mixture
  3. additionHCl (aq) (2N, 25 mL) was added to the reaction mixture, and it
  4. customformed a clear biphasic mixture
  5. extractionextracted with EtOAc (2×75 mL)
  6. washThe combined organic layers were washed with water (25 mL) and saturated NaCl (50 mL)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0ccecc2792f48cb885c956fef121498
Source dataset
uspto-grants-2014_10
Patent number
US08871943B2

Reaction notes

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