Propargyl alcohol → 3-(3,4-Dichlorophenyl)-2-propynal

Participants

Reaction Steps

Pyridinium chlorochromate (24.23 g; 112.4 mmol; 2 eq) was added to a stirred solution of 3-(3,4-dichlorophenyl)prop-2-yn-1-ol (11.3 g; 56.2 mmol) in dichloromethane (225 mL) at room temperature. The mixture was stirred for 3.5 h until TLC (2:1 heptane/ethyl acetate) indicated the disappearance of the starting propargyl alcohol. The mixture was then filtered through a bed of celite, and the filter cake was rinsed with dichloromethane (150 mL). The dichloromethane was concentrated using a rotary evaporator to give the desired product (5.48 g; 27.5 mmol; 49%) which was used in the next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.20 (d, 1H) 7.31 (d, 1H) 7.51 (s, 1H) 9.43 (s, 1H).

Provenance & Evidence