Phenylglyoxylic Acid → HCID 59487971, compound

Participants

Reaction Steps

In a 50 ml dry three-neck-flask, 4.9 g (33.0 mmol) of phenylglyoxylic acid are dissolved under nitrogen in solution, of 1.45 g (36.3 mmol) of NaOH in 6 ml water at 0° C. 5.0 g (16.5 mmol) dibutyltin dichloride in 15 ml THF are added dropwise in the course of 0.5 h at 0° C. The emulsion is slowly warmed to room temperature, then heated to 40° C. and stirred for 30 min. The formed oil is separated off and the aqueous phase is extracted several times with methylene chloride. The oil and the methylene chloride phases are combined, dried over MgSO4, filtered and concentrated. The resulting oil is dissolved with heating in 20 ml of pentane and 10 ml of toluene and cooled. The crystals are filtered off at 0° C., dissolved in 20 ml of acetonitrile and extracted with 10 ml of heptane. The acetonitrile solution is concentrated affording 2.6 g of the title product as a yellow oil, which is recrystallized from 10 ml of pentane and 4 ml of ortho-xylene. The white crystals melt at 82-84° C. The structure of the product is further confirmed by 1H-NMR- and 13C-NMR-spectra.

Provenance & Evidence