Carbon Dioxide → 4-Chloro-2-(trifluoromethyl)benzoic acid

HRID 343000Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[Mg].[C:14](=[O:16])=[O:15].Cl>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:14]([OH:16])=[O:15])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-chloro-2-trifluoromethyliodobenzene (100 g) in ether was added to a suspension of magnesium (8 g) in ether at a such a rate as to maintain the mixture at reflux. The mixture was stirred at reflux for 1 hour and then cooled to 0° C. Carbon dioxide was then passed into the stirred mixture for 3 hours. Hydrochloric acid (2M) was added and the resulting layers separated. The organic layer was washed with water and then extracted into aqueous sodium carbonate solution and this aqueous extract was acidified to pH 1 and extracted with ether. The ether layer was washed with saturated sodium chloride solution, dried (anhydrous magnesium sulphate) and the solvent evaporated to give 4-chloro-2-trifluoromethylbenzoic acid (57.1 g) as a brown solid, m.p. 106.5°-108° C.

Workup

temperatureto maintain the mixture
temperatureat reflux
temperatureat reflux for 1 hour
customthe resulting layers separated
washThe organic layer was washed with water
extractionextracted into aqueous sodium carbonate solution
extractionthis aqueous extract
extractionextracted with ether
washThe ether layer was washed with saturated sodium chloride solution
dry with materialdried (anhydrous magnesium sulphate)
customthe solvent evaporated

Sources & evidence

ORD record: ord-0718be8cb0b84232a6871ffb8e797c61
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859283

Reaction notes

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