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 for 3 hours at this temperature and then, after returning to room temperature, ethyl acetate is added, separation is carried out by settling, the aqueous phase is acidified with a 1N aqueous hydrochloric acid solution, extracted with ethyl acetate, 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, filtered off and dried. There is obtained 0.4 g of (S)-2-(2-methoxyphenyl)propionic acid in the form of white crystals melting at 102° C. [α]D20=+84.6° (c=1, CHCl3).

Provenance & Evidence