Any suggestions for a suitable oxidation?
I'm doing a university project where I have to use 2-pyridine carbaldehyde, however, we only had picolinic acid. Hence I thought about first reducing it to the alcohol and performing an oxidation to the aldehyde (i.e. lab didn't have DIBAL and I couldn't use LiAlH4 so I first made the picolinate ester and reduced with NaBH4 in MeOH/NaOMe). Now it's quite essential that we do not get substantial overoxidation to picolinic acid, as I have a limited amount of the alcohol but we may not use any of the chromium oxidants (PCC, PDC) and they are not a fan of DMP; cannot even use DCM or chloroform.
I actually considered this approach because we performed a similar pathway for oxidation of 4-methyl benzyl alcohol to the aldehyde using bleach in a biphasic reaction, but I feel quite stupid for not considering that the pyridine alcohol is quite soluble in water which was no problem with the benzyl alcohol. I thought I could just add a large amount of NaCl to saturation, but I have noticed that the pyride compounds really still tend to partition significantly in the waster layer and I cannot permit overoxidizing 50% of my alcohol, so I'm wondering whether you have suggestions.
It's quite strange in the sense that they have some quite exotic compounds; also we can work under nitrogen with ice bath, so this is all fine but they sometimes do not have standard compounds (today I had to make NaOMe myself) like MnO2, so any super niche reagents are not accessible.