Sodium Borohydride + Vanillin Explain why the product is soluble in aqueous NaOH, but precipitates upon addition of HCl?

EBK A SMALL SCALE APPROACH TO ORGANIC L
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ISBN:9781305446021
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Chapter39: Preparation Of An Α, Β-unsaturated Ketone Via Michael And Aldol Condensation Reactions
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Sodium Borohydride + Vanillin

Explain why the product is soluble in aqueous NaOH, but precipitates upon addition of HCl? 

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