Water → 3-Fluoro-4-methoxyphenol
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[F:1][C:2]1[CH:3]=[C:4](C(=O)C)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].ClC1C=CC=C(C(OO)=[O:21])C=1.O[Li].O.O>C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[C:4]([OH:21])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9][F:1][C:2]1[CH:3]=[C:4](C(=O)C)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].ClC1C=CC=C(C(OO)=[O:21])C=1.O[Li].O.O>C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[C:4]([OH:21])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]
A solution of 3′-fluoro-4′-methoxyacetophenone (10 g; 59 mmol) and m-chloroperbenzoic acid (50% purity; 30 g; 89 mmol) in CH2Cl2 (300 mL) was stirred at RT overnight. The solution was washed with saturated aqueous Na2CO3, then filtered through a pad of SiO2 (CH2Cl2 as eluent) and finally chromatographed (SiO2; hex:EtOAc 4:1) to give the crude product (3′-fluoro-4′-methoxy phenyl acetate; 63 g). A solution of this crude material and LiOH.H2O (5 g; 120 mmol) in MeOH:H2O (100 mL of a 9:1 mixture) was stirred at RT overnight. Volatiles were removed in vacuo, and the residue was partitioned between excess aqueous 1 M HCl and EtOAc (aqueous layer pH˜3). The aqueous phase was extracted with EtOAc (2×). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give 3-fluoro-4-methoxy phenol (6.1 g; 72%) as an oil.
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