Abstract
A method is described for the simple and rapid formation of saturated fatty aldehydes from the corresponding acid chlorides. It is not suitable for the preparation of unsaturated aldehydes because of the partial reduction and positional and geometrical isomerization of the double bond in the chain.
Highlights
LONG-CHAAINLDEHYDES are not readily available commercially. Difficulties encountered during their preparation by the Rosenmund reduction [1] and by the Sakurai and Tanabe modification of the Rosenmund reduction [2] led us to study these reactions and to make further modifications which allow the synthesis of pure fatty aldehydes with 10-20 carbon atoms in high yield
The product was examined by thin-layer chromatography (TLC) and gasliquid chromatography (GLC)
The Sakurai and Tanabe procedure, which used A’,i\-dimethylaniline to neutralize the HCl, gave good yields of pure longerchain fatty aldehydes, e.g. arachidaldehyde and stearaldehyde, shorter-chain fatty aldehydes so prepared contained considerable amounts of volatile impurities: more than 10% for palmitaldehyde and more than 50% for decanaldehyde
Summary
Additions of the N,N-dimethylaniline or the N,N-dimethylacetamide (0.5 ml) as HC1 neutralizer and later of the acid chloride (300 mg) obtained from The Hormel Institute (Austin, Minn.) were made by means of a syringe through the sidearm. The reaction, was run at room temperature, constantly stirred, and kept under slight pressure (2-4 mm Hg) by periodically raising the leveling bulb. The Sakurai and Tanabe procedure, which used A’,i\-dimethylaniline to neutralize the HCl, gave good yields of pure longerchain fatty aldehydes, e.g. arachidaldehyde and stearaldehyde, shorter-chain fatty aldehydes so prepared contained considerable amounts of volatile impurities: more than 10% for palmitaldehyde and more than 50% for decanaldehyde.
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