[OH:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:14][C:15]([OH:17])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[C:23](=O)(O)[O-].[Na+]>CO>[OH:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:14][C:15]([O:17][CH3:23])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1The crude 2-(1-(3-hydroxyphenyl)cyclohexyl)acetic acid 105.C (1.01 g) was dissolved in MeOH (15 mL) and a catalytic (˜10 drops) amount of concentrated sulfuric acid was added. The mixture was then refluxed for 16 hours and then cooled to room temperature. The reaction was then made basic with saturated sodium bicarbonate solution and concentrated to dryness. The residue was then dissolved in EtOAc and water and the layers were separated. The aqueous layer was extracted (2×75 mL) with EtOAc. The combined organic layers were then washed with brine (1×75 mL) and dried over magnesium sulfate. The crude product was purified by medium pressure chromatography (silica, 0 to 15% EtOAc: DCM) to give methyl 2-(1-(3-hydroxyphenyl)cyclohexyl)acetate 105 (560 mg, 52% yield). MS ESI (pos.) m/e: 266.2 (M+H2O)+.
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