Carbon Dioxide → Phenylpropiolic Acid

(4,7-Diphenyl-1,10-phenanthroline)bis[tris(p-fluorophenyl)phosphine]copper(I) nitrate (10.9 mg, 0.01 mmol) and cesium carbonate (391 mg, 1.20 mmol) were placed in a flask. The reaction vessel was then flushed with nitrogen and closed by means of a septum. Degassed DMF (3.00 ml) was subsequently added and the resulting mixture was stirred for 5 minutes at room temperature. After repeated evacuation and admission of CO2 into the reaction vessel, phenylacetylene (110 μL, 1.00 mmol) was injected. The reaction mixture was stirred at 35° C. and 5 bar of CO2 pressure in a steel autoclave for 12 hours. After the reaction time had expired, the reaction mixture was cooled to room temperature, diluted with water and extracted three times with 100 ml each time of n-hexane. The aqueous fraction was admixed with dilute HCl (1N, 10.0 ml), forming a colorless solid which was filtered off and purified further by recrystallization from water and ethanol. The purified colorless solid (143 mg, 98%) having a melting point of 133-134° C. could be identified as the desired reaction product.

1. customThe reaction vessel was then flushed with nitrogen
2. customclosed by means of a septum
3. additionDegassed DMF (3.00 ml) was subsequently added
4. stirringThe reaction mixture was stirred at 35° C.
5. temperaturethe reaction mixture was cooled to room temperature
6. extractionextracted three times with 100 ml each time of n-hexane
7. customforming a colorless solid which
8. filtrationwas filtered off
9. custompurified further by recrystallization from water and ethanol
10. customreaction product

ORD record

ord-9d2a667839e544c5942ceb816c1e9742

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073844B2