Carbon Dioxide → 1-Methyl-9-fluorenecarboxylic acid

Participants

Reaction Steps

A solution of 1-methylfluorene (3.8 g, 21.1 mmol) in 100 mL of THF at -78° C. was charged with n-butyl lithium (3.5M solution in hexane, 6.29 ml, 22.0 mmol). The reaction mixture was stirred for 15 min, then CO2 gaseous (5 g, 113.6 mmol) was introduced via cannula over a period of 15 min. The reaction mixture was warmed up to room temperature and stirring was continued until no color was apparent (approximately 2 hr). The slurry was diluted with water (100 mL) and ethyl acetate (50 mL). The layers were separated, the water layer was washed with ethyl acetate (3×50 mL), then acidified with conc. HCl. The precipitate was collected, washed with water and dried to give 1-methyl-9-fluorenecarboxylic acid (4.02 g, 84.8%).

Provenance & Evidence