Английская Википедия:3-Hydroxybutanal

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Шаблон:Short description Шаблон:Chembox

In organic chemistry, 3-hydroxybutanal (acetaldol, aldol) is an organic compound with the formula Шаблон:Chem2 and the structure Шаблон:Chem2. It is classified as an aldol (Шаблон:Chem2) and the word "aldol" can refer specifically to 3-hydroxybutanal. It is formally the product of the dimerization of acetaldehyde (Шаблон:Chem2). A thick colorless or pale-yellow liquid, it is a versatile and valuable intermediate with diverse impacts.[1] The compound is chiral although this aspect is not often exploited.

Production

Acetaldehyde dimerizes upon treatment with aqueous sodium hydroxide:[1]

Шаблон:Chem2

This is the prototypical aldol reaction.

Reactions and uses

Dehydration of 3-hydroxybutanal gives crotonaldehyde. Distillation of 3-hydroxybutanal is sufficiently forcing to effect this conversion:[1]

Шаблон:Chem2

Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol:

Шаблон:Chem2

This diol is a precursor to 1,3-butadiene, precursor to diverse polymers.

Polymerization of 3-hydroxybutanal is also spontaneous, but can be stopped with the addition of water.

Aldol has been used in making perfumes and in ore flotation.[2]

Former or niche uses

It was formerly used in medicine as a hypnotic and sedative.[3]

See also

References

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