Hydrochloric Acid → Salicylic Acid

Temperature

25 °C

Under nitrogen, 2.00 g (9.95 mmol) of 2-bromobenzoic acid was combined with 10 g of H2O. 1.11 g (10.45 mmol) of Na2CO3 was then added. The mixture was heated to reflux with stirring for 30 min, remaining under a nitrogen atmosphere. Another 1.58 g (14.92 mmol) of Na2CO3 was added to the reaction mixture and reflux was continued for 30 min. Separately, 22 mg of CuBr2 and 28 mg of rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (Ligand F) were combined with 2 mL H2O under nitrogen to give a deep purple solution. This solution was added to the stirred reaction mixture via syringe at 80° C. under nitrogen and stirred for 1 h at 80° C. After cooling to 25° C., the reaction mixture was acidified with 15% HCl, producing a white precipitate. The white precipitate was filtered and washed with water. After drying, a total of 1.34 g (9.7 mmol, 98% yield) salicylic acid was collected. The purity was determined by 1H NMR to be about 99%.

1. temperatureThe mixture was heated
2. temperatureto reflux
3. temperaturereflux
4. waitwas continued for 30 min
5. customto give a deep purple solution
6. additionThis solution was added to the stirred reaction mixture via syringe at 80° C. under nitrogen
7. stirringstirred for 1 h at 80° C
8. customproducing a white precipitate
9. filtrationThe white precipitate was filtered
10. washwashed with water
11. customAfter drying

ORD record

ord-6fecd6e10505435d8f2759ee15292187

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07335791B1