p-Toluenesulfonic acid → HCID 15819505, compound

1.6 g of 3-(6-acetoxymethyl-1,3-benzodioxole-5-yl)propionic acid was dissolved in 100 ml of methanol. A catalytic amount of p-toluenesulfonic acid was added to the solution and the mixture was heated under reflux for 4 h and 15 min. The solvent was distilled off from the reaction mixture. A solution of 1 g of sodium hydroxide in a mixture of 5 ml of water and 45 ml of ethanol was added to the residue and the mixture was heated under reflux for 20 min. The reaction mixture was concentrated. 200 ml of ethyl acetate and 200 ml of water were added to the concentrate. The mixture was acidified with concentrated hydrochloric acid. The layers thus formed were separated. The product was washed with water three times and then dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 1.25 g of the intended compound in the form of a white powder.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 4 h and 15 min
3. distillationThe solvent was distilled off from the reaction mixture
4. additionA solution of 1 g of sodium hydroxide in a mixture of 5 ml of water and 45 ml of ethanol
5. additionwas added to the residue
6. temperaturethe mixture was heated
7. temperatureunder reflux for 20 min
8. concentrationThe reaction mixture was concentrated
9. addition200 ml of ethyl acetate and 200 ml of water were added to the concentrate
10. customThe layers thus formed
11. customwere separated
12. washThe product was washed with water three times
13. dry with materialdried over anhydrous sodium sulfate
14. distillationThe solvent was distilled off

ORD record

ord-62fa804c743a4425be24fb2bcd7b1b5c

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05475024