[CH:1]([C:3]1[CH:11]=C(C(O)=O)[C:6]([OH:12])=[CH:5][CH:4]=1)=[O:2].[C:13](=O)([O-])[O-].[K+].[K+].CI.[C:21]([O:24][CH2:25]C)(=[O:23])[CH3:22].CCCCCC>CC(C)=O>[CH3:13][O:12][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:11][C:22]=1[C:21]([O:24][CH3:25])=[O:23]Combine 5-formylsalicylic acid (5.0 g, 30.1 mmol), potassium carbonate (16.6 g, 120.4 mmol), and methyl iodide (34.06 g, 240 mmol) in acetone (20 mL). Heat to reflux. After 12 hours, cool and extract five times with ethyl acetate. Combine the organic layers and extract with brine. Dry over MgSO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate/hexane 1/1 to give methyl 2-methoxy-5-formylbenzoate: Rf=0.44 (silica gel, 1/1 ethyl acetate/hexane).
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