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13.15 : Carboxylic Acids to Primary Alcohols: Hydride Reduction

Carboxylic acids, upon reaction with strong reducing agents such as lithium aluminum hydride followed by hydrolysis, undergo reduction to form primary alcohols.

Carboxylic acid reduction with LiAlH4 to primary alcohol, chemical reaction diagram, organic synthesis.

Weaker reducing agents like lithium tri-tert-butoxyaluminum hydride or diisobutylaluminum hydride cannot reduce carboxylic acids to primary alcohols.

Carboxylic acids can also be reduced to primary alcohols by using borane in the tetrahydrofuran solvent. The main advantage of using borane in reducing a carboxylic acid is that this reagent can selectively reduce carboxylic acid to primary alcohol in the presence of other reducible functional groups, such as a ketone or a nitro group.

Bh3 reduction reaction diagram showing conversion of ketone to alcohol using THF solvent.

Tags

Carboxylic AcidsPrimary AlcoholsHydride ReductionLithium Aluminum HydrideLithium Tri tert butoxyaluminum HydrideDiisobutylaluminum HydrideBoraneTetrahydrofuranSelective ReductionKetoneNitro Group

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