How could 1,4-butanediol be converted to 1,4-butandial (succinic aldehyde)? I thought of simple oxidation with CuO but apparently it yields gamma-butyryllactone according to erowid (https://erowid.org/archive/rhodium/chemistry/gbl.synthesis.microgram.html#refs) and this paper: (https://onlinelibrary.wiley.com/doi/abs/10.1002/14356007.a04_495). Could increasing the pH result in the formation of 1,4-butandial?

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    $\begingroup$ Alternatively, I am quite sure that PCC would stop at the aldehyde stage. Here, a complex diol with a 4-carbon chain is oxidized to dialdehyde with the "similar" PDC sciencedirect.com/science/article/abs/pii/… $\endgroup$ – The_Vinz May 26 '19 at 9:51
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    $\begingroup$ DMSO-based oxidation is another valid and widely cited in literature approach (eg. Swern Oxidation) $\endgroup$ – The_Vinz May 26 '19 at 9:57
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    $\begingroup$ Difficult stuff to handle as it is prone to polymerisation. Best stored as 2,5-dimethoxytetrahydrofuran which is functionally equivalent for synthetic purposes. $\endgroup$ – Waylander May 26 '19 at 10:10
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    $\begingroup$ True; speaking of that, wouldn't it be easier to convert easily accesssible tetrahydrofuran into 2,5-dimethoxytetrahydrofuran directly? How could I substitute a methoxy group into 2nd and 5th position? $\endgroup$ – Francis L. May 26 '19 at 10:41
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    $\begingroup$ THF can be chlorinated at low temps with UV light below -10C to 2,5-dichloro-THF (ref here chempap.org/file_access.php?file=311a109.pdf) and then reacted with MeONa/MeOH to give 2,5-dimethoxy-THF. I would not call this an easy option, given that 2,5-dimethoxy-THF is widely commercially available $\endgroup$ – Waylander May 26 '19 at 11:19

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