IMPROVED SYNTHESIS OF CYANOHYDRIN PHOSPHATES AND ITS REACTION MECHANISM

Abstract

Cyanohydrin phosphates 2a–2c were prepared in high yield from ketones (or aldehyde), diethyl phosphorochloridate, and sodium cyanide by using acetonitrile as solvent. GC analysis proved that the two reactions of cyanohydrin sodium with diethyl phosphorochloridate and with diethyl phosphorocyanidate resulted in the formation of cyanohydrin phosphates.

Keywords:

• Cyanohydrin phosphate
• phosphorochloridate
• phosphorocyanidate

Notes

∗The mixture of DEPC and acetone (without sodium cyanide) was stirred at room temperature for 3 h, but GC/MS analysis showed no changes during the entire process.

∗∗Cyanohydrin sodium can be easily prepared by sodium and cyanohydrin (preparation see Org. Synth., II, 7, 1943).

∗∗∗Acetonitrile was chosen mainly due to its good properties in liquid-solid two-phase reactions according to our prior experiments. ⁶