Ethanol → Canthaxanthin

HRID 842350

Reaction equation

HRID 842350 reaction equation
[CH3:1][C:2]1CC[CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:40])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:39])=[CH:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](\[CH3:38])/[CH:22]=[CH:23]/[CH:24]=[C:25](\[CH3:37])/[CH:26]=[CH:27]/[C:28]1[C:33]([CH3:35])([CH3:34])[CH2:32][CH2:31][CH2:30][C:29]=1[CH3:36].C(Cl)(Cl)Cl.[OH2:45].[CH2:46]([OH:48])[CH3:47]>>[CH3:1][C:2]1[C:46](=[O:48])[CH2:47][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:40])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:39])=[CH:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](\[CH3:38])/[CH:22]=[CH:23]/[CH:24]=[C:25](\[CH3:37])/[CH:26]=[CH:27]/[C:28]1[C:33]([CH3:35])([CH3:34])[CH2:32][CH2:31][C:30](=[O:45])[C:29]=1[CH3:36]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 962WaterHCID 6212ChloroformHCID 5280489Beta-Carotene

Product 1

HCID 5281227CanthaxanthinYield 85%

Procedure

Into a flask was charged 0.5 gm of β-carotene and 10 ml of chloroform. The mixture is stirred to form a solution. Into this solution was charged 1.6 ml of the oxidant solution described in example 1. The mixture was stirred for 1.5 hours to complete the reaction. The phases were separated and the organic phase was washed with water once and evaporated to yield a residue that was dissolved in 10 ml of warm ethanol. This ethanol solution was added slowly to 50 ml of water to form a precipitate which was filtered and dried to yield 85% yield of canthaxanthin of approximately 80% purity.

Workup

  1. customto form a solution
  2. stirringThe mixture was stirred for 1.5 hours
  3. customthe reaction
  4. customThe phases were separated
  5. washthe organic phase was washed with water once
  6. customevaporated
  7. customto yield a residue that
  8. customto form a precipitate which
  9. filtrationwas filtered
  10. customdried

Sources & evidence

ORD record
ord-bbaa20909ddd4b8a880e98272433b08a
Source dataset
uspto-grants-2002_04
Patent number
US06372946B1

Linked notes

Loading…