Sodium Chlorate → Canthaxanthin

HRID 2057736

Reaction equation

HRID 2057736 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:41])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:40])=[CH:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](/[CH:23]=[CH:24]/[CH:25]=[C:26](/[CH:28]=[CH:29]/[C:30]1[C:36]([CH3:38])([CH3:37])[CH2:35][CH2:34][C:32](=[O:33])[C:31]=1[CH3:39])\[CH3:27])\[CH3:22].Cl([O-])(=O)=[O:43].[Na+]>C(Cl)(Cl)Cl.O.II>[CH3:39][C:31]1[C:32](=[O:33])[CH2:34][CH2:35][C:36]([CH3:38])([CH3:37])[C:30]=1/[CH:29]=[CH:28]/[C:26](/[CH3:27])=[CH:25]/[CH:24]=[CH:23]/[C:21](/[CH3:22])=[CH:20]/[CH:19]=[CH:18]/[CH:17]=[C:16](\[CH3:40])/[CH:15]=[CH:14]/[CH:13]=[C:12](\[CH3:41])/[CH:11]=[CH:10]/[C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][C:7](=[O:43])[C:2]=1[CH3:1]

Participants

6

Reactant 2

HCID 516902Sodium ChlorateHCID 5281236all-trans-Echinenone

Product 1

HCID 5281227CanthaxanthinYield 65.3%

Reagents, catalysts & solvents 3

HCID 807IodineCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent2×

Conditions

Temperature
-20 °C

Procedure

100 mg of echinenone are dissolved in 10 ml of chloroform under a nitrogen atmosphere and are oxidized with 100 mg of sodium chlorate in 1 ml of water after having added 2 mg of iodine dissolved in 1 ml of chloroform. After stirring for 24 hours at -20° C., 67 mg of canthaxanthin having an all-trans content of 81% are obtained.

Sources & evidence

ORD record
ord-648c87607f584ecda96f203161e74617
Source dataset
uspto-grants-1980_07
Patent number
US04212827

Linked notes

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