Hydrochloric Acid → HCID 178436265, compound

Participants

Reaction Steps

Mercaptoacetic acid (9.2 g, 0.1M) was added over 5 minutes to a stirred solution of potassium hydroxide (12.3 g, 0.22M) in methanol (40 ml). 4-Vinylbenzyl chloride (15.25 g, 0.1M) was then added over 5 minutes during which an exothermic reaction ensued and the mixture turned yellow. The mixture was stirred at room temperature for 5 minutes, then it was heated under reflux on a steam-bath for 1 hour. After being allowed to cool, the mixture was concentrated under reduced pressure to leave a yellow solid. 3M Hydrochloric acid (100 ml) was added to the solid and this mixture was stirred at room temperature for 2 hours. The resulting cream solid was filtered off, washed with water and dried, 20.0 g. The solid was stirred with 60-80 petroleum-ether (60 ml) for 2 hours then the resulting white solid was filtered off, washed with 60-80 petroleum-ether and dried to give 4-vinylbenzylthioacetic acid, 17.8 g (85%). The negative ion mass spectrum was consistent with the structure of the required product as was the 1H nmr spectrum, which also indicated high purity. LCMS showed a single component of the requisite molecular weight.

Provenance & Evidence