i performed photocatalytic benzyl alcohol to benzaldehyde oxidation using acetonitrile as solvent and O2 as oxidant with my prepared catalyst. for analysis, i did H-NMR of the crude mixture after catalytic done only simply sucked a small amount of it and mixed to d-CHCl3.

Unfortunately, chem-shift of -CH near C=O (10.03, for benzaldehyde as product) did not appear even for 4 h reaction time.

Do i prepare H-MNR sample in correct way?

Thanks

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