Chloroacetyl chloride → HCID 88454312, compound

Participants

Reaction Steps

In a 1 L round bottom flask equipped with a magnetic stirrer, thermometer and condenser is placed 50 g (0.15 mol) of trans-2-(2'-benzyloxy-5'-chlorophenyl)cyclohexanol. This is dissolved in 200 ml of methylenechloride, and then 18 g (0.16 mol) of chloracetyl chloride is added followed by 0.14 g (0.001 mol) of 4-dimethylaminopyridine. The mixture is heated to reflux and monitored by TLC (20% ethyl acetate, hexane). After 4 hours TLC shows the reaction to be complete, it is cooled to room temperature and 200 ml of saturated sodium bicarbonate is added. The reaction mixture is stirred rapidly for another 3 hours. The organic phase is then separated, dried with anhydrous potassium carbonate, filtered and evaporated under reduced pressure to yield 70 g of an amber oil. This oil is dissolved in 100 ml of hexane from which it crystallizes to afford 47 g of an off-white solid trans-2-(2'-benzyloxy-5'-chloro-phenyl)cyclohexyl chloroacetate, which is used directly in the next step.

Provenance & Evidence