Ethylene → HCID 89464145, compound

Participants

Reaction Steps

Oxalyl chloride (14.7 g) was added over 10 minutes to a solution of 3,4,5-trimethoxyphenylacetic acid (23.8 g) in DCM (400 ml) and DMF (5 drops). The mixture was stirred at ambient temperature for 18 hours. The solvents were removed under vacuum to give an orange oil which was redissolved in DCM (100 ml) and then added to a solution of aluminium chloride (43.3 g) in DCM (1.0 L) at 5° C. The mixture was stirred at 5° C. for 10 minutes before ethylene gas was gently bubbled through the mixture for 1 hour. The crude reaction mixture was poured on to ice/water and stirred vigorously for 20 minutes. The organic phase was separated and washed with a aqueous 2N HCl solution, saturated aqueous NaHCO3 solution and brine, dried (MgSO4) and filtered. The solvents were removed under vacuum to give a dark oil that was redissolved in ethyl acetate (60 ml). Sodium bisulfite (28.6 g) in water (60 ml) was added to the mixture, stirring for 18 hours. A precipitate was removed by filtration, washed with ethyl acetate and dried under vacuum.

Provenance & Evidence