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

HRID 1242354Notes

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 redissolved in 70 ml of water; 60 ml of cold 8 N aqueous HCl was then added and the acid extracted with three portions of 250 ml of ethyl acetate; the combined organic phases were washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Thereby, 25.1 g of the title product was obtained as 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 redissolved in 70 ml of water
addition60 ml of cold 8 N aqueous HCl was then added
extractionthe acid extracted with three portions of 250 ml of ethyl acetate
washthe combined organic phases were washed with water and brine
dry with materialdried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-34f6045d0cb6428791c4385c67bf7254
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Reaction notes

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