Acetic acid t-butylthioester
A mixture of tBuSH 33.8mL (300mmol) and acetyl chloride 22.4mL (315mmol) was cooled to 0C. Aluminum chloride 400mg (3mmol) was added, the flask was equipped with a reflux condenser with a Dryerite-filled gas outlet tube. The flask was placed on ambient water bath and the mixture was stirred for 1 hour (the HCl gas evolution ceased within 20 min). The reaction was quenched by addition of KF solid, 525mg (9 mmol). The mixture was distilled at atmospheric pressure. After a small front fraction (3 mL), a pure product distilled at 131-132C.
Y = 34.18g of a colorless liquid (86% th)