Water → Ubiquinol 10

HRID 597849Notes

Reaction equation

HRID 597849 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][CH2:24]/[CH:25]=[C:26](/[CH2:28][CH2:29]/[CH:30]=[C:31](/[CH2:33][CH2:34]/[CH:35]=[C:36](/[CH2:38][CH2:39]/[CH:40]=[C:41](/[CH2:43][CH2:44]/[CH:45]=[C:46](/[CH2:48][CH2:49]/[CH:50]=[C:51](/[CH2:53][CH2:54]/[CH:55]=[C:56](/[CH2:58][CH2:59][CH:60]=[C:61]([CH3:63])[CH3:62])\[CH3:57])\[CH3:52])\[CH3:47])\[CH3:42])\[CH3:37])\[CH3:32])\[CH3:27])\[CH3:22])\[CH3:17].O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CCCCCCC>[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].[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][CH2:24]/[CH:25]=[C:26](/[CH2:28][CH2:29]/[CH:30]=[C:31](/[CH2:33][CH2:34]/[CH:35]=[C:36](/[CH2:38][CH2:39]/[CH:40]=[C:41](/[CH2:43][CH2:44]/[CH:45]=[C:46](/[CH2:48][CH2:49]/[CH:50]=[C:51](/[CH2:53][CH2:54]/[CH:55]=[C:56](/[CH2:58][CH2:59][CH:60]=[C:61]([CH3:63])[CH3:62])\[CH3:57])\[CH3:52])\[CH3:47])\[CH3:42])\[CH3:37])\[CH3:32])\[CH3:27])\[CH3:22])\[CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 5281915Ubidecarenone

Product 2

HCID 5280344Ubiquinol 10HCID 5281915Ubidecarenone

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
2 °C

Procedure

In 1,000 g of heptane, 100 g of ubiquinone (product of Kaneka Corporation) was dissolved at 25° C. Under stirring (stirring power: 0.3 kW/m3), an aqueous solution prepared by adding 1,000 ml of water to 100 g of sodium dithionite (purity: 75% or higher) was gradually added as a reducing agent and the reduction reaction was carried out at 25° C. and pH 4 to 6. After the lapse of 2 hours, the aqueous layer was removed from the reaction mixture and the heptane layer was washed 6 times with 1,000 g of a degassed saturated saline. This heptane layer was cooled to 2° C. under stirring (stirring power: 0.3 kW/m3) to give a white slurry. The whole of the above operation was carried out under a nitrogen atmosphere. The slurry obtained was filtered under reduced pressure and the obtained wet crystals were washed serially with cold heptane, cold ethanol, cold water, cold ethanol, and cold heptane in that order (the temperature of each cold solvent used for washing was 2° C.). The wet crystals were then dried under reduced pressure (20 to 40° C., 133 to 400 Pa) to recover 93 g of white dry crystals (yield: 92.8 mole %, purity: 99.3%). The ubiquinol/ubiquinone ratio of the product crystals was 99.6/0.4. As analyzed by HPLC in the conventional manner, the steric configurations of both the ubiquinol and ubiquinone obtained were (all-E)-isomers.

Workup

  1. stirring(stirring power: 0.3 kW/m3)
  2. customan aqueous solution prepared
  3. additionwas gradually added as a reducing agent
  4. customthe reduction reaction
  5. customwas carried out at 25° C.
  6. customAfter the lapse of 2 hours, the aqueous layer was removed from the reaction mixture
  7. washthe heptane layer was washed 6 times with 1,000 g of a degassed saturated saline
  8. stirringunder stirring
  9. stirring(stirring power: 0.3 kW/m3)
  10. customto give a white slurry
  11. customThe slurry obtained
  12. filtrationwas filtered under reduced pressure
  13. washthe obtained wet crystals were washed serially with cold heptane, cold ethanol, cold water, cold ethanol, and cold heptane in that order (the temperature of each cold solvent
  14. washfor washing
  15. customwas 2° C.
  16. customThe wet crystals were then dried under reduced pressure (20 to 40° C., 133 to 400 Pa)
  17. customto recover 93 g
  18. customof white dry crystals (yield: 92.8 mole %, purity: 99.3%)

Sources & evidence

ORD record
ord-d3bcf5266303472aa2819e7299792bc9
Source dataset
uspto-grants-2011_03
Patent number
US07897169B2

Reaction notes

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