Thioglycolic Acid → [{2-(1,3-Benzodioxol-5-yl)-2-propyl}thio]acetic acid

600 ml of benzene, 59.5 g of mercaptoacetic acid and a catalytic amount of D-10-camphorsulfonic acid were added to 97 g of 2-(1,3-benzodioxol-5-yl)-2-propanol. The obtained mixture was heated under reflux for 4 hours and distilled to remove the solvent. The pH of the residue was adjusted to 10 with a 1N aqueous solution of sodium hydroxide. The resulting mixture was washed with ethyl acetate. 4N hydrochloric acid was added to the mixture under cooling with ice to acidify the aqueous layer. The resulting mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated to obtain a crude crystal. This crude crystal was recrystallized from diisopropyl ether to obtain 62.70 g of the title compound as a colorless crystal.

1. temperatureThe obtained mixture was heated
2. temperatureunder reflux for 4 hours
3. distillationdistilled
4. customto remove the solvent
5. washThe resulting mixture was washed with ethyl acetate
6. addition4N hydrochloric acid was added to the mixture
7. temperatureunder cooling with ice
8. extractionThe resulting mixture was extracted with chloroform
9. washThe organic layer was washed with water
10. dry with materialdried over anhydrous magnesium sulfate
11. filtrationfiltered
12. concentrationThe filtrate was concentrated
13. customto obtain a crude crystal
14. customThis crude crystal was recrystallized from diisopropyl ether

ORD record

ord-e2f9642b70ef488280af7e44c21ac864

Source dataset

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05292901