Butanal → HCID 20550298, compound

HRID 2058521Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][Mg]Br.[CH:20](=[O:24])[CH2:21][CH2:22][CH3:23]>>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][CH:20]([OH:24])[CH2:21][CH2:22][CH3:23]

Participants

Reactant 2

HCID 261Butanal

HCID 178419645HCID 178419645, compound

Product 1

HCID 20550298HCID 20550298, compound

Procedure

For example, according to the above-cited British patent, one starts from 10-(2-tetrahydropyranyloxy-)dec-1-ynyl magnesium bromide, which is reacted with butyraldehyde to obtain 14-(-2-tetrahydropyranyloxy-)-tetradec-5-yn-4-ol, which is then dehydrated to 2-(-tetradec-11-en-9-ynyloxy-)-tetrahydropyranyl(cis, trans mixture); the latter, after acetylation and reduction, provides a cis-cis and cis-trans mixture of 9,11-tetradecadienyl-acetate. To obtain the desired cis-trans compound, a difficult and expensive separation of the isomers is required.

Sources & evidence

ORD record: ord-9b66a78c50cd4710a418e265feb3f4e6
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04317905

Reaction notes

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