Reaktion #48776

Reaktionsgleichung

methyl 3-[(1S)-2-methoxy-(1-methylethyl)oxy]-5-{[4-(methylsulfonyl)phenyl]oxy}benzoate

sodium hydroxide

→

desired compound

Ausbeute 83.0%

3-{(1S)-2-Methoxy-(1-methylethyl)oxy}-5-{[4-(methylsulfonyl)phenyl]oxy}benzoic acid

Ausbeute 83.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeMost of the organic solvent was removed in vacuo
2. 2
   workup.ADDITIONthe remaining solution was diluted with water (150 mL)
3. 3
   Extraktionextracted with ethyl acetate (2×100 mL)
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigeevaporated

Vorschrift

A solution of methyl 3-[(1S)-2-methoxy-(1-methylethyl)oxy]-5-{[4-(methylsulfonyl)phenyl]oxy}benzoate (60.9 mmol) in THF (400 mL) was treated with a solution of 1M sodium hydroxide (125 mmol), and the reaction mixture stirred for 13 hours at ambient temperature. Most of the organic solvent was removed in vacuo, and the remaining solution was diluted with water (150 mL). The resulting aqueous solution was acidified to pH4 with 1M citric acid solution, and extracted with ethyl acetate (2×100 mL). The extracts were combined, washed with brine, dried (MgSO4), and evaporated to give the desired compound (83% yield).

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