Sulfur Dioxide → HCID 596766, compound

Participants

Reaction Steps

432 mg of silver tetrafluoborate and 305 mg of hydroquinone dimethyl ether are first introduced into a flask fitted with a cold finger. After fitting a dropping funnel sealed by a serum cap and equipped with a pressure compensating device, the apparatus is evacuated 5 times under a waterpump vacuum and is subsequently filled with dry nitrogen. Sulphur dioxide was then condensed in the apparatus at -20°C until the volume of the solution is 40 ml. A solution of 2-chloropropanal-N-cyclohexylnitrone in 10 ml of absolute methylene chloride is then introduced into the dropping funnel and is added dropwise over the course of 2 hours to the vigorously stirred sulphur dioxide solution. The temperature is kept at -10°C for a further 6 hours and the sulphur dioxide is then pumped off in a waterpump vacuum. Towards the end, fresh methylene chloride is added in portions in order to keep the volume at between 10 and 20 ml. After filtering off the silver chloride (through Celite, with rinsing with 3×15 ml of methylene chloride), the filtrate is vigorously stirred with 60 ml of 5% strength hydrochloric acid for 5 hours and then separated off. After washing with concentrated sodium bicarbonate solution and concentrated sodium chloride solution (each wash solution being extracted with 2×10 ml of methylene chloride), and drying with sodium sulphate, the solution is evaporated and the yellow-brown oil which remains is filtered through 10 g of aluminium oxide IV (column filled with hexane and eluted with 30 ml of hexane and 80 ml of 4:1 hexane-benzene). The concentrated eluate is distilled in a rotating bulb tube at 90°C/2 mm Hg. α-(2,5-Dimethoxy-phenyl)-propionaldehyde is thus obtained.

Provenance & Evidence