(E)-4,4-Dimethoxybut-2-enal (2) is a key intermediate for the synthesis of 4-hydroxynonenal (HNE) that has been extensively investigated for its role in Alzheimer's disease pathology. In the preparation of 2, hydrolysis of (E)-1,1,4,4-tetramethoxybut-2-ene (1) resulted in both 2 and fumaraldehyde (3) in previous literature reports. We have developed a selective monohydrolysis method which gives 2 without forming 3: A solution of 1 in mixed solvent of H2O and acetone (1:3) with suspended Amberlyst-15 was stirred at 0 �C for 2 h, filtered to remove Amberlyst-15, basified with Na2CO3, and stored at -20 �C for 16 h. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/239nm/uploads/3755_figure_1.jpg' alt='' />

Selective monohydrolysis of (E)-1,1,4,4-tetramethoxybut-2-ene

242nd National Meeting (2011)

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