Acetyl chloride → HCID 86744602, compound

Participants

Reaction Steps

To a solution of 3.5 g (0.01 mol) of rac.-(R,*S*)α-(hydroxy)-4-methoxyphenyl-β-[(2-oxo -2-phenYlethYl)thio]benzenepropanamide in 130 mL of methylene chloride and 4.4 mL of pyridine was added dropwise at ice-bath temperature a solution of 1.1 g (0.014 mol) of acetyl chloride in 25 mL of methylene chloride. The mixture was stirred at this temperature for one hour then at room temperature for 17 hrs and diluted with water. The aqueous suspension was extracted with methylene chloride and the combined organic solutions were washed with water and dried (MgSO4). Removal of the solvent gave the crude ester, which after crystallization from ethyl acetate afforded 2.9 g (74%) of rac.-(S,*R*)-α-(acetyloxy)-4-methoxyphenyl -β-[(2-oxo-2-phenylethyl) thio]benzenepropanamide, mp 122°-123°.

Provenance & Evidence