[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH2:5][C:6]([O:14][CH3:15])([CH:11]=[CH:12][CH:13]=1)[C:7](OC)=[O:8].[H-].C([Al+]CC(C)C)C(C)C.CO>C1(C)C=CC=CC=1.CCCCCC>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH2:5][C:6]([O:14][CH3:15])([CH:11]=[CH:12][CH:13]=1)[CH:7]=[O:8]To a -78° to -100° solution of 1.0 mol of 3-methoxyisophthalic acid dimethyl ester in 1-10 l of toluene is slowly added 1.0 mol of diisobutylaluminum hydride as a 1 M solution in n-hexane. The reaction is stirred for 3 hours after the addition and then quenched by the addition of 10 mol of anhydrous methanol. The reaction is allowed to warm to room temperature and stirred until a filterable precipitate forms. The reaction is filtered and the filtrate evaporated to a residue. The residue is purified by crystallization, distillation or chromatography to yield 3-methoxyisophthalaldehydic acid methyl ester.
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