Methanol → 2-(3-Fluorophenoxy)acetic acid
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[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH2:6][C:7]([O:9]CC)=[O:8].CO.O.O.[OH-].[Li+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH2:6][C:7]([OH:9])=[O:8][F:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH2:6][C:7]([O:9]CC)=[O:8].CO.O.O.[OH-].[Li+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH2:6][C:7]([OH:9])=[O:8]To a solution of ethyl 3-fluorophenoxy-acetate (2 g, 10 mmol) in 24 mL of a 1:1:1 solution of MeOH:H2O:THF is added lithium hydroxide monohydrate (2.25 g, 54 mmol). The solution is stirred for 16 hours. After this time, the solution is concentrated under reduced pressure to ⅓ of its volume. The remaining solution is acidified to pH=3 with 1N HCl (aq.). The aqueous solution is extracted with EtOAc. The organic layer is washed with a saturated solution NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated to give the product (1.65 g, 9.7 mmol) as a white solid. 1H NMR (CDCl3, 300 MHz) δ9.8 (bs, 1H), 7.28 (m, 1H), 6.69 (m, 3H), 4.70 (s, 2H).
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