4-Toluenesulfonyl chloride → (3-Chloroprop-1-yn-1-yl)benzene

Participants

Reaction Steps

1-Phenyl-1-propyn-3-ol (5 g), 5.1 g of tosyl chloride and 20 ml of pyridine were stirred at room temperature for 1 hour. The reaction mixture was poured into 100 ml of ice water and extracted with ethyl acetate. The oil layer was washed with 1 N hydrochloric acid and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away. The residue was purified by silica gel column chromatography (ethyl acetate:hexane 1:5) to give 2.54 g of 3-phenyl-2-propynyl chloride as a pale yellow, oily substance.

Provenance & Evidence