Carbon Dioxide → Benzoic acid, 3-(1-methylethyl)-

HRID 1610693Notes

Reaction equation

[Mg].II.[CH:4]([C:7]1[CH:8]=[C:9](Br)[CH:10]=[CH:11][CH:12]=1)([CH3:6])[CH3:5].BrCCBr.[C:18](=[O:20])=[O:19].Cl>O1CCCC1.O>[CH:4]([C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[C:18]([OH:20])=[O:19])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 70 °C

Procedure

While stirring a solution of powdery magnesium (3.33 g, 137 mmol) and iodine (one crumb) in tetrahydrofuran (10 ml), a solution of 3-isopropylbromobenzene (10.91 g, 54.80 mmol) and 1,2-dibromoethane (10.3 g, 54.8 mmol) in tetrahydrofuran (100 ml) was dropwise added slowly. After completion of the dropwise addition, the mixture was stirred at 70° C. for 1 hr. The reaction solution was cooled to −78° C., and pulverized dry ice (10 g) was carefully added. The reaction solution was gradually warmed to room temperature with stirring. The reaction solution was diluted with water, acidified with conc. hydrochloric acid, and extracted twice with ethyl acetate. The solvent of the recovered organic layer was evaporated under reduced pressure to give a crude product of 3-isopropylbenzoic acid as a yellow liquid.

Workup

additionAfter completion of the dropwise addition
temperatureThe reaction solution was cooled to −78° C.
additionwas carefully added
temperatureThe reaction solution was gradually warmed to room temperature
stirringwith stirring
extractionextracted twice with ethyl acetate
customThe solvent of the recovered organic layer was evaporated under reduced pressure

Sources & evidence

ORD record: ord-65efc7f73ba9418aa715cdae44e12f8e
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982348B2

Reaction notes

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