Sodium Thiosulfate → Ubiquinol 10

HRID 1038292Notes

Reaction equation

HRID 1038292 reaction equation
[CH3:1][C:2]1[C:8](=[O:9])[C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[C:4](=[O:5])[C:3]=1[CH2:14]/[CH:15]=[C:16](/[CH2:18][CH2:19]/[CH:20]=[C:21](/[CH2:23]C/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)\C)\C)\C)\C)\C)\[CH3:22])\[CH3:17].[O-]S([O-])(=S)=O.[Na+].[Na+]>CCCCCC>[CH3:1][C:2]1[C:8]([OH:9])=[C:7]([O:10][CH3:11])[C:6]([O:12][CH3:13])=[C:4]([OH:5])[C:3]=1[CH2:14]/[CH:15]=[C:16](/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])\[CH3:17]

Participants

4

Reactant 2

HCID 24477Sodium ThiosulfateHCID 5281915Ubidecarenone

Product 1

HCID 5280344Ubiquinol 10Yield 264.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

30 g of ubiquinone (MW: 863.36) was dissolved in 300 ml of hexane. While the solution was stirred at room temperature, 300 ml of a 10% (w/v) sodium hyposulfite solution was poured to the solution. The mixture was stirred at room temperature for 2 hours. The mixture was all introduced into a separating funnel, and the hexane layer was collected. The remaining aqueous layer was then extracted twice each with 50 ml of hexane, and the extract was combined with the previously collected hexane layer. The hexane layer was washed six times each with 50 ml of a deaerated saturated saline solution, thereby obtaining a transparent hexane layer. After hexane was removed under a reduced pressure, nitrogen purging was performed for day and night, resulting in 29.5 g of a cream colored solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. additionall introduced into a separating funnel
  3. customthe hexane layer was collected
  4. extractionThe remaining aqueous layer was then extracted twice each with 50 ml of hexane
  5. washThe hexane layer was washed six times each with 50 ml of a deaerated saturated saline solution
  6. customobtaining a transparent hexane layer
  7. customAfter hexane was removed under a reduced pressure, nitrogen purging
  8. waitwas performed for day and night

Sources & evidence

ORD record
ord-096e7f8d2b224b6ca116216745fe6215
Source dataset
uspto-grants-2013_10
Patent number
US08551509B2

Reaction notes

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