Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methylglyoxal | HCID 880 | — |
| Reactant | Triethylenetetramine | HCID 5565 | — |
| Reactant | Glyoxal | HCID 7860 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 178418385 | HCID 178418385 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 11298738 | HCID 11298738 | 40% |
Reaction Steps
A 40% strength solution of 61.53 g of pyruvaldehyde in water (341.8 mmol) in 20 ml of water is added by slow dropwise addition INto a solution of 50 g (341.8 mmol) of triethylenetetraamine in 800 ml of distilled water cooled to 2° C. On completion of addition, the reaction mixture is adjusted to ambient temperature and 81.36 g (683.6 mmol) of benzotriazole are added in a single portion. A solution of glyoxal (40% in water) (341.8 mmol) in 200 ml of methanol is then added by slow dropwise addition. After 2 h of stirring at ambient temperature, 25.85 g (683.6 mmol) of NaBH4 are added in small portions. After 2 h of stirring at ambient temperature, the methanol is evaporated and 50 g of KOH pellets are added to the residue. The solution is then extracted with three 1.5 l portions of chloroform. After drying over MgSO4 and evaporation of the solvents, (IIb) is isolated in the form of an orange oil (28.50 g; yield=40%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07659393B2 |
|---|
| Source dataset | uspto-grants-2010_02 |
|---|
| ORD ID | ord-abb7738ca13944a39b9006034db7d773 |
|---|
| Source note | uspto-grants-2010_02 |
|---|