N,N-Dimethylaniline → HCID 12438231, compound

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Reaction Steps

60 gms. (0.4 moles) of DL-mandelic acid are dissolved in 50 ml. of tetrahydrofuran. 50 gms. (0.4 moles) of dimethylaniline are added and the mixture is cooled to -20°. 45 gms. (0.5 moles) of methyl chloroformate are added with vigorous stirring. After 30 minutes, the reaction mixture is poured into 500 ml. of ice-water and extracted with ethyl acetate. The organic phase is washed with 100 ml. of 2N HCl solution and concentrated after drying over sodium sulfate. A light oil is obtained which crystallizes on standing overnight. The product, DL-α-[(methoxycarbonyl)oxy]-phenylacetic acid is recrystallized from cyclohexane to obtain white crystals, m.p. 103°-105°.

Provenance & Evidence