Acetone → Squalane

HRID 1576598Notes

Reaction equation

[CH:1]#[CH:2].[CH3:3][C:4]([CH3:6])=O>>[CH3:3][CH:4]([CH2:6][CH2:1][CH2:2][CH:4]([CH2:6][CH2:1][CH2:2][CH:4]([CH2:6][CH2:1][CH2:2][CH2:3][CH:4]([CH2:6][CH2:1][CH2:2][CH:4]([CH2:6][CH2:1][CH2:2][CH:4]([CH3:6])[CH3:3])[CH3:3])[CH3:2])[CH3:3])[CH3:3])[CH3:1]

Participants

Reactant 2

HCID 180Acetone3×

HCID 6326Acetylene

Product 1

HCID 8089Squalane

Procedure

Ethynylation of 194 g of citronelliodene acetone was carried out with acetylene in the same manner as in example 20 except that citronellidene acetone was used in place of pseudoionone and 278 g of a crude product was thus obtained. This product was subjected to oxydative-coupling, hydrogenation and hydrogenolysis in sequence in the same manner as in example 20 and squalane was thus obtained in a yield of 36.3 % from citronellidene acetone to squalane.

Workup

customwas thus obtained

Sources & evidence

ORD record: ord-1df100cf3da846e19b08e1147018cc11
Source dataset: uspto-grants-1976_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03981930

Reaction notes

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