[NorthWardVale]

For a research project, I am attempting to synthesise vanillyl alcohol. In order for me to syntehsize my wanted product, I need to reduce vanillin with a metal hydride. I have been looking into using LiAlH₄ and/or LiBH₄, but I am concerned about their reactivity with water. The process Im going to attempt involves dissolving vanillin in NaOH, and then using the hydride to reduce it, followed by adding HCl to neutralise it. My concern is the LiAlH₄ or LiBH₄ will react with the water that the NaOH is dissolved in and/or the water produced during the neutralisation of the NaOH. Is this a valid concern, and if it is, what other metal hydride reducing agents can I get my hands on easily? I need a minimum of 2, as I am planning to use NaBH4 as well and want minimum of 3 options.

[Vidya]

You can not use LiAlH4 because it is very reactive and H - immediately reacts with water to form H2.
But LiBH4 or NaBH4 is not so reactive and I think you can use it for reduction even in the presence of water.

[NorthWardVale]

What about NaAlH₄

[Vidya]

Actually it is BH4 - and it can be with Na+ or Li + and in both ways it is less reactive than AlH4-.