Hydrochloric Acid → Propanoic acid, 2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]-

HRID 235558Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([F:22])[C:5]([O:8][C:9]2[CH:21]=[CH:20][C:12]([O:13][CH:14]([CH3:19])[C:15]([O:17]C)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[OH-].[Na+].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([F:22])[C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH:14]([CH3:19])[C:15]([OH:17])=[O:16])=[CH:20][CH:21]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 67.0 g (0.206 mole) of methyl 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionate, 350 ml of dioxan and 250 ml of 1N sodium hydroxide solution is stirred for 2 hours at 40° C. The reaction mixture is poured into a mixture of ice and 150 ml of 2N hydrochloric acid and extracted twice with ethyl acetate. The extracts are washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated by evaporation, affording 63.6 g (99% of theory) of 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionic acid with a melting point of 95°-97° C.

Workup

extractionextracted twice with ethyl acetate
washThe extracts are washed with a saturated solution of sodium chloride
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-ad24f3bb72fe41cbb480228ea42be9a7
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640703

Reaction notes

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