Propargyl alcohol → 3-(p-Tolyl)propiolaldehyde

Participants

Reaction Steps

Pyridinium chlorochromate (22.1 g; 102.6 mmol; 2 eq) was added to a stirred solution of 3-p-tolylprop-2-yn-1-ol (7.5 g; 51.3 mmol) in dichloromethane (200 mL) at room temperature under nitrogen. The mixture was stirred for 4 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 (100 mL). The dichloromethane was concentrated using a rotary evaporator to give the desired product (4.22 g; 29.3 mmol; 57%) which was used in the next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.39 (s, 3 H) 7.20 (d, 2H) 7.50 (d, 2H) 9.41 (s, 1H).

Provenance & Evidence