2-Mercaptoethanol → Butanoic acid, 3-oxo-, 2-mercaptoethyl ester

Participants

Reaction Conditions

Reaction Steps

In a 300 ml. round bottom flask fitted with a thermometer, mechanical stirrer, Dean Stark trap and reflux condenser was placed 25.0g.(0.32 mole) of 2-mercaptoethanol. This was stirred and heated to 130° C.; 45.4g. (0.32 mole) of 2,2,6-trimethyl-1,3-dioxen-4-one (TKD) was added dropwise at a uniform rate over the period of one hour. Heating was continued for 1/2 hour; acetone distillate was collected in the Dean Stark trap. After distillate collection was completed, the mixture was distilled under vacuum and the portion boiling at 110°-115° C.(at 5 mm. Hg.) was collected to give a colorless liquid of mercaptoethylacetoacetate. The yield was about 90% based on starting material. The product was identified by NMR spectroscopy.

Provenance & Evidence