Pyridine → HCID 19909132, compound

Participants

Reaction Steps

15.2 gm (0.10 mole) dl-mandelic acid was dissolved in 50 ml acetone and placed in one of two 125 ml additional funnels attached to a 250 ml three-necked round bottom flask charged with 8.0 gm (0.10 mole) pyridine in 50 ml acetone cooled in an ice water bath. The other addition funnel was charged with 16.3 gm (0.10 mole) octanoyl chloride. The contents of the two addition funnels were simultaneously added dropwise over 20 minutes to the stirred/cooled pyridine solution. The reaction was removed by rotary evaporation. The residue was dissolved in 200 ml diethyl ether and this solution was extracted with 5×150 ml 5% HCl, and then washed with 1×200 ml deionized water. The organic layer was dried over Na2SO4, filtered and the solvent removed by rotary evaporation. After drying in vacuo there remained 28.2 gm of oil. GC and 13C NMR determined this material to be 83.1% of the desired product, for an overall 84.2% yield.

Provenance & Evidence