Water → [2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic Acid

HRID 890447Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH2:8][C:9]#N)=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:3]=1.[OH-:21].[Na+].[OH2:23]>C(O)CC>[CH3:1][C:2]1[C:7]([CH2:8][C:9]([OH:23])=[O:21])=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 25 g (90 mmol) of the above prepared [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetonitrile, 20 g of sodium hydroxide (500 mmol), 60 ml of water and 250 ml of propanol was stirred vigorously at 100° C. Hydrolysis was complete after 2 hours. The reaction mixture was then evaporated to dryness and the residue was dissolved in 70 ml of water; then, 60 ml of cold 8 N aqueous HCl were added and the compound was extracted with three portions of 250 ml of ethyl acetate; the combined organic phases were washed with water and brine, dried with anhydrous sodium sulfate and evaporated. 25.1 g (93.9%) of [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic acid were obtained as a pale yellow solid.

Workup

additionA mixture of 25 g (90 mmol) of the
customHydrolysis
customThe reaction mixture was then evaporated to dryness
dissolutionthe residue was dissolved in 70 ml of water
additionthen, 60 ml of cold 8 N aqueous HCl were added
extractionthe compound was extracted with three portions of 250 ml of ethyl acetate
washthe combined organic phases were washed with water and brine
dry with materialdried with anhydrous sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-f3cbcf9b3ae34e158c31bed315bb61c0
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995263B2

Reaction notes

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