2,6,10,15,19,23-Hexamethyltetracosa-11,13-diyne-10,15-diol → Squalane

HRID 596563Notes

Reaction equation

HRID 596563 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][CH:7]([CH3:32])[CH2:8][CH2:9][CH2:10][C:11]([CH3:31])(O)[C:12]#[C:13][C:14]#[C:15][C:16]([CH3:29])(O)[CH2:17][CH2:18][CH2:19][CH:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH3:3]>[Pd].CCCCCCC>[CH3:26][CH:24]([CH2:23][CH2:22][CH2:21][CH:20]([CH2:19][CH2:18][CH2:17][CH:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][CH2:8][CH:7]([CH2:6][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1])[CH3:32])[CH3:31])[CH3:29])[CH3:27])[CH3:25]

Participants

4

Reactant 1

HCID 214273422,6,10,15,19,23-Hexamethyltetracosa-11,13-diyne-10,15-diol

Product 1

HCID 8089SqualaneYield 85.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8900HeptaneSolvent

Procedure

To 100 ml of n-heptane was dissolved 50 g of 2,6,10,15,19,23-hexamethyltetracosa-11,13-diyne-10,15-diol which was prepared in the same manner as in example 5 and 2.5 g of 3 % palladium on active carbon was added. The mixture was hydrogenated at 50° C under a hydrogen pressure of 3 ~ 5 kg/cm2. The product was subjected to dehydration, hydrogenation and distillation in the same manner as in example 4 to give 40.6 g of squalane.

Workup

  1. additionwas added
  2. customwas hydrogenated at 50° C under a hydrogen
  3. distillationThe product was subjected to dehydration, hydrogenation and distillation in the same manner as in example 4

Sources & evidence

ORD record
ord-fd418ceb12f04b7fad48c39743d71078
Source dataset
uspto-grants-1977_03
Patent number
US04011277

Reaction notes

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