video tutorial Two more attempts to make vanillyl nitrile

Name: video tutorial - Two more attempts to make vanillyl nitrile
Uploaded: 2025-12-11T09:03:44.347Z
Duration: 14 min 35 s
Description: In fact we've done this in a previous video with exactly these two reagents....We prepared this in a previous video by reacting sodium acetate and acetyl chloride, so check

Goal: transform vanillin (an aldehyde) into the corresponding nitrile (vanillyl nitrile).
Strategy: form the oxime intermediate from vanillin and hydroxylamine, then attempt dehydration to the nitrile using dehydrating agents.
Experiment 1: dehydration with acetic anhydride in the presence of a base (pyridine) led to formation of an O-acetyl vanillin oxime and no nitrile; reaction did not yield the desired product.
Experiment 2: dehydration of pure vanillin oxime with phosphorus pentoxide in dichloromethane also failed; hydrolysis returned to vanillin, producing a mixture rather than the nitrile.
Conclusion: these routes did not provide the desired nitrile; highlights the difficulty of selectively dehydrating oximes to nitriles and competition from hydrolysis; discusses broader synthetic planning challenges and mentions considering algorithmic approaches; notes a break and planned continuation later.