Hello everyone
I want to convert methyl salicylate into salicylaldehyde, I want to find the safest and cheapest method. I know NaBH4 can convert aromatic ester into alcohol, but is it possible that NaBH4 can reduce ester to aldehyde?
DIBAL-H is very expensive for me
Conversion of esters to aldehydes can be accomplished by reduction with diisobutyl aluminium hydride.
Stephen reduction involves the preparation of aldehydes. Nitriles react with anhydrous stannous chloride in presence of dry hydrogen chloride gas followed by their hydrolysis to form aldehydes. Rosenmund reduction is the catalytic hydrogenation of acid chlorides to aldehydes. Diisobutyl aluminium hydride is used to reduce α−βunsaturated esters to the corresponding allylic alcohols.
Best wishes
it is often difficult to stop the reduction at the aldehyde stage and you may end up with a mixture of aldehyde and alcohol. I found that it is often easier to reduce the ester all the way down to the alcohol and then oxidise to the aldehyde.
Simple and cheap oxidations like Swern or Moffat are worth a go.
best of luck
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