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

HRID 1160717Notes

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.C1COCC1.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

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 MeOH, 50 mL THF and 50 mL 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 EtOAc (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

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

Sources & evidence

ORD record: ord-ba393651e44046dc8a21669150893fbd
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816534B2

Reaction notes

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