Sodium Hydroxide → 2-Methyl-2-(4-trifluoromethyl-2-pyridyloxy)propionic Acid

HRID 2104280Notes

Reaction equation

HRID 2104280 reaction equation
[CH3:1][C:2]([O:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=1)([CH3:7])[C:3]([O:5]C)=[O:4].[OH-].[Na+]>CO.O1CCCC1.O>[CH3:7][C:2]([O:8][C:9]1[CH:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:12]=[CH:11][N:10]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 22270531Methyl 2-Methyl-2-(4-trifluoromethyl-2-pyridyloxy)propionate

Product 1

HCID 222704912-Methyl-2-(4-trifluoromethyl-2-pyridyloxy)propionic Acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-methyl-2-(4-trifluoromethyl-2-pyridyloxy)propionate (Step B, 7.5 g, 29 mol) in 50 mL of methanol, 50 mL of tetrahydrofuran and 50 mL of water was added sodium hydroxide (2.3 g, 57 mmol). After stirring at 50° C. for 5 h, the reaction mixture was partially concentrated, and was added 2 M hydrochloric acid to pH >2. The resulting mixture was extracted with ethyl acetate (2×200 mL), and the combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 8.28 (d, 1H), 7.17 (d, 1H), 7.05 (s, 1H), 1.70 (s, 6H).

Workup

  1. concentrationthe reaction mixture was partially concentrated
  2. additionwas added 2 M hydrochloric acid to pH >2
  3. extractionThe resulting mixture was extracted with ethyl acetate (2×200 mL)
  4. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d92308541d4c4f2098433027602740db
Source dataset
uspto-grants-2009_08
Patent number
US07576239B2

Reaction notes

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