Carbon Dioxide → Benzoic acid, 3-ethyl-

Participants

Reaction Conditions

Reaction Steps

Magnesium turnings (829 mg, 34.1 mmol) were placed in an oven-dried 50 mL RBF and heated three times under high vacuum, then filled with nitrogen. The flask was sealed with a rubber septum and a pressure release system. Anhydrous THF (6.0 mL) and 1-bromo-3-ethylbenzene (297 mg, 1.6 mmol) were added. The reaction mixture was heated to 50-60° C. for 5 min. 1-Bromo-3-ethylbenzene (5.812 g, 31.4 mmol) was dissolved in anhydrous THF (12.0 mL) and added drop-wise via syringe maintaining 50-60° C. The reaction mixture was stirred for 2 h cooling to room temperature. The septum was replaced by a balloon with carbon dioxide and stirred for 16 h at room temperature. The reaction was quenched with a few grams of dry ice, acidified with hydrochloric acid (2M, 50 mL) and extracted with diethylether (2×100 mL). The combined organic layers were washed with a solution of sodium hydroxide (1M, 100 mL). The organic layer was disposed. The aqueous layer was acidified with hydrochloric acid (2M, 100 mL) and extracted with diethylether (2×100 mL). The combined organic of this extraction were dried (MgSO4), filtered and concentrated in vacuo. The title compound was obtained as pale pink crystalline solid (2.698 g, 54%).

Provenance & Evidence