Lithium Hydroxide → (S)-2-(2-Methoxyphenyl)propanoic acid

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Reaction Steps

1.52 g of lithium hydroxide are added to a solution, cooled to +5° C., of 4.1 g of (4S,5S)-4-methyl-5-phenyl-3-[(S)-2-(2-methoxyphenyl)propionyl]oxazolidin-2-one in 60 cm3 of tetrahydrofuran and 30 cm3 of water. The reaction mixture is stirred at this temperature for 3 hours and then, after returning to room temperature, ethyl acetate is added, the phases are separated by decanting, the aqueous phase is acidified with 1N aqueous hydrochloric acid solution and extracted with ethyl acetate, and the organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is recrystallized from hexane, drained and dried. 0.4 g of (S)-2-(2-methoxyphenyl)propionic acid is obtained in the form of white crystals melting at 102° C. [α]D20 =+84.6° (C=1; CHCl3)

Provenance & Evidence