C([O:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=1)=O.C([O-])([O-])=O.[K+].[K+].Cl>CO.O>[CH3:14][O:13][C:6]1[CH:5]=[C:4]([OH:3])[CH:9]=[C:8]([O:10][CH3:11])[C:7]=1[CH3:12]To a solution of 3,5-dimethoxy-4-methylphenyl formate (2.9 g, 14.8 mmol) in wet MeOH (81 mL) was added K2CO3 (8.1 g, 58.6 mmol). The mixture was stirred for 2 hrs at room temperature then H2O (2-3 mL) was added. After stirring for 21 hrs, the mixture was diluted with H2O, acidified with 6M HCl to pH 3-4, and extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-35% EtOAc-hexanes) gave 3,5-dimethoxy-4-methylphenol as an impure yellow powder (0.71 g, 29% yield).
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