Methylglyoxal → HCID 11298738, compound

Participants

Reaction Conditions

Reaction Steps

A 40% strength solution of 6.16 g of pyruvaldehyde in water (34.2 mmol) in 10 ml of ethanol is added by slow dropwise addition into a solution of 5 g (34.2 mmol) of triethylenetetraamine in 30 ml of ethanol cooled to 0° C. On completion of addition, the reaction mixture is adjusted to ambient temperature and 8.15 g (68.5 mmol) of benzotriazole are added in a single portion. A solution of 4.97 g of glyoxal (40% in water) (34.2 mmol) in 5 ml of ethanol is added by slow dropwise addition. After 2 h of stirring at ambient temperature, the solution is cooled to 0° C. and 2.59 g (68.5 mmol) of NaBH4 are added in small portions. After returning to ambient temperature, the reaction medium is stirred for 2 hours, the ethanol is evaporated, 50 ml of water and 6.5 g of KOH pellets are added to the residue. The solution is then extracted with two 300 ml portions of chloroform. After drying over MgSO4 and evaporation of the solvents, (IIb) (a mixture of several isomers) is isolated in the form of an orange oil (4.84 g; yield=68%).

Provenance & Evidence