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Chemistry · Ch 12 — Aldehydes, Ketones and Carboxylic Acids

Preparation of aldehydes only from esters

12.4.3

Preparation of aldehydes only from esters

Aliphatic or aromatic ESTERS can be reduced specifically to ALDEHYDES using diisobutylaluminium hydride, DIBAl-H (also written AlH(i-Bu)2): R-CO-O-R' with AlH(i-Bu)2, then H3O+ on workup, gives R-CHO + R'-OH. The reaction is deliberately carried out at a low temperature -- around 195 K -- specifically to stop the newly-formed aldehyde from being reduced any further, all the way down to …