Conversion of acid chlorides to aldehydes using LiAlH(O-tBu)3

by James

Description: Addition of the bulky reducing agent lithium tri-t-butoxy aluminum hydride [LiAlH(O-tBu)3] to acid chlorides results in the formation of aldehydes.
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Notes: The nucleophile here is the hydride ion, which adds once to the acid halide, resulting in the aldehyde.

Examples:

Notes: The byproduct of these reactions are LiCl and Al(O-t-Bu)3

Mechanisms: Addition of the hydride to the acid chloride (Step 1, arrows A and B) results in a tetrahedral intermediate, which undergoes elimination of chloride ion (Step 2, arrows C and D) to give the neutral aldehyde.

Notes:

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{ 2 comments… read them below or add one }

Stephanie B

Would it be possible to reverse this reaction and convert an aldehyde into an acid chloride?

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james

Not in one step, no. You’d need to oxidize it to a carboxylic acid and then convert it to the acid chloride. Those are two different steps.

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