[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[C:3]=1O.[CH3:10]I.[C:12]([O-:15])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:10][O:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([CH3:1])[C:3]=1[O:15][CH3:12]In a round bottom flask, 3-methyl catechol (5.0 g, 40.3 mmol), MeI (22.3 g, 157.1 mmol), and K2CO3 (18.9 g, 136.9 mmol) were dissolved in acetone (20.0 ml). The reaction mixture was stirred at room temperature for 1 h, then at 60° C. for overnight. The reaction mixture was concentrated and chromatographed on silica gel using EtOAc/Hexane (5:95). A pale yellow liquid was isolated in 100% (6.13 g). The characterization of the compound matched previous report: Xing, L.; Wang, X.; Cheng, X.; Zhu, R.; Liu, B.; Hu, Y. Tetrahedron Letters 2007, 63, (38), 9382-9386.
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