Thioglycolic Acid → iso-Butyldisulfanyl-acetic acid

Participants

Reaction Steps

To 11 g (50 mmol) of 2-,2′-dipyridyl disulfide and 10.5 mL (75 mmol) of triethyl amine in 100 mL of tetrahydrofuran at 0° C. as added 3.5 mL (50 mmol) of mercaptoacetic acid in 5 mL of tetrahydrofuran. The ice bath was removed and after one hour 5.5 mL (50 mmol) iso-butyl thiol was added. The reaction was allowed to stir overnight at ambient temperature before diluting with ether and washing three times with 1N aqueous HCl. The product was then extracted into 10% aqueous NaOH. The aqueous phase was washed twice with ether and then acidified with HCl to pH ˜3.5. The product was extracted with ether, dried with Na2SO4, filtered and evaporated under reduced pressure to give a crude product. This material was distilled by Kugelrohr distillation to give 3.0 g (17 mmol, 33%) of partially purified product. This material was used in the next step without further purification.

Provenance & Evidence