Butanal → 2-Ethyl-3-hydroxyhexanal

HRID 1788820Notes

Reaction equation

[CH2:1]=[CH:2][CH3:3].[CH:4](=[O:8])[CH2:5][CH2:6][CH3:7].[CH:9](=[O:13])C(C)C>>[CH3:1][CH2:2][CH2:3][CH:9]([OH:13])[CH:5]([CH:4]=[O:8])[CH2:6][CH3:7]

Participants

Reactant 3

HCID 261Butanal

HCID 6561Isobutyraldehyde

HCID 8252Propylene

Product 1

HCID 103242-Ethyl-3-hydroxyhexanal

Procedure

This compound is usually prepared by the hydroformylation of propene yielding a reaction mixture which contains n-butanal, as well as i-butanal and other reaction products. The pure n-butanal is separated from the reaction mixture by distillation and is subsequently subjected to aldolisation to form the corresponding butyraldol. This product is heated, water splits off, and 2-ethyl-hexenal is formed. This compound is then hydrogenated in the presence of appropriate catalysts to form the desired 2-ethyl-hexanol which is then purified in a multi-step distillation process.

Workup

customThe pure n-butanal is separated from the reaction mixture by distillation

Sources & evidence

ORD record: ord-f4b2f6b895ea49ca973111d860418a32
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04684750

Reaction notes

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