(S)-(+)-O-Acetyl-L-mandelic acid synthesis
- Product Name:(S)-(+)-O-Acetyl-L-mandelic acid
- CAS Number:7322-88-5
- Molecular formula:C10H10O4
- Molecular Weight:194.18
17199-29-0
108-24-7
7322-88-5
Example 1; Preparation of (S)-2-acetoxy-2-phenylacetic acid 1; To a round bottom flask containing mandelic acid (15 g, 111 mmol) was added 100 mL of acetic anhydride. After stirring for 5 min, 10 mL of anhydrous ether and a catalytic amount of DMAP were added sequentially. the reaction mixture was stirred at room temperature for 16 h. The reaction was carried out at room temperature. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure to give an amorphous solid. The solid was dissolved with EtOAc (50 mL) and washed sequentially with 1N HCl (2 x 10 mL), water (2 x 10 mL) and saturated saline (10 mL). The organic phase was dried with anhydrous MgSO4, filtered and concentrated under reduced pressure. Purification by column chromatography with hexane solution of 20% EtOAc as eluent gave the target product (15.8 g, 81 mmol) in 73% yield.The Rf value was 0.54 by TLC (unfolding reagent ratio 1:1 hexane:EtOAc).1H NMR (CDCl3, δ): 11.5 (s, 1H), 7.43 (m, 5H), 5.99 ( s, 1H), 2.20 (s, 3H).
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