ChemicalBook CAS DataBase List Coenzyme Q10

Coenzyme Q10 synthesis

9synthesis methods

Product Name:Coenzyme Q10
CAS Number:303-98-0
Molecular formula:C59H90O4
Molecular Weight:863.34

Phenol, 3-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-yl]-4,5,6-trimethoxy-2-methyl-

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303-98-0
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Yield:303-98-0 100%

Reaction Conditions:

with iron(III) chloride in dichloromethane;acetonitrile at 0 - 5; for 0.5 h;Product distribution / selectivity;

Steps:

3; 8

Example 3 Oxidation of 2-hydroxy-3,4,5-trimethoxy-6-decaprenyl-toluene In a 100 ml flask 1.09 g (0.91 mmol) of 73.3% 2-hydroxy-3,4,5-trimethoxy-6-decaprenyl- toluene were dissolved in 4.1 ml of dichloromethane and 4.1 ml acetonitrile at 0⁰C. To this solution 2.46 g FeCl₃ ? 6 H₂O (9.0 mmol, commercial from Riedel de Haen) in 8.2 ml of acetonitrile were added at 0-5⁰C. After 30 minutes at 0-5⁰C, 60 ml deionised water were added and the orange emulsion after addition of 60 ml 5% aqueous NaHCO₃ solution was extracted with 250 ml of ether. The water layer was extracted with 60 ml of ether. The combined ether phases were dried over Na₂SO₄ and concentrated at 35°C under reduced pressure (20 to 10 mbar). The crude product (orange oil, 1.09 g, 100 %) was analysed by HPLC to be CoQlO; E/Z-ratio 95.8:4.2. The oxidation of the "trimethoxy-CoQIO" with FeCl₃-OH₂O to from CoQlO was effected as follows: EPO In a 100 ml flask 1.09 g of "trimethoxy-CoQlO" (0.91 mmol, 73.3 %) were dissolved in 4.1 ml of dichloromethane and 4.1 ml of acetonitrile at 0°C. To this solution 2.46 g of FeCl₃ hexahydrate (9.0 mmol, commercial from Riedel de Haen) in 8.2 ml of acetonitrile were added at 0-5⁰C. After half an hour at 0-5°C, 60 ml of deionised water were added and the orange emulsion after addition of 60 ml NaHCO₃ solution (5%) was extracted with 250 ml of ether. The water layer was again extracted with 60 ml of ether. The combined ether phases were dried over Na₂SO₄ and concentrated at 35°C (20 -> 10 mbar). The crude product, CoQlO (orange oil, 1.09 g, 100 %), was analysed by HPLC. E/Z-ratio = 95.8:4.2.