Carbon Dioxide → 2,6-diisopropylbenzoic acid

HRID 1756769Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1I)([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.[C:25](=[O:27])=[O:26].[OH-].[Na+]>C(OCC)C.O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[C:25]([OH:27])=[O:26])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5.09 g (17.7 mmol) of 2, 6-diisopropylphenyl iodide in 70 ml of dry ethyl ether was dropwise added 1.6M solution of n-butyllithium in hexane (11.1 ml, 17.8 mmol) at -20° C. The reaction mixture was allowed to warm at 0° C., stirred for 1 hour and poured onto about 100 g of pulverized dry ice. The mixture was allowed to warm gradually to room temperature, mixed with 50 ml of water and the aqueous layer was made alkaline with aqueous sodium hydroxide. The organic layer was separated, and the aqueous layer was washed with ethyl ether, acidified With conc. hydrochloric acid and extracted with ethyl ether. The extract was washed with saturated saline, dried over anhydrous magnesium sulfate, and the solvent evaporated to give 2.53 g of 2, 6-diisopropylbenzoic acid as white solid.

Workup

customat -20° C
temperatureto warm gradually to room temperature
customThe organic layer was separated
washthe aqueous layer was washed with ethyl ether
extractionextracted with ethyl ether
washThe extract was washed with saturated saline
dry with materialdried over anhydrous magnesium sulfate
customthe solvent evaporated

Sources & evidence

ORD record: ord-04f7a9d7a4fd48079b1ac35638ab2f7f
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05442060

Reaction notes

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