Methanol → Lycopene

HRID 55911

Reaction equation

HRID 55911 reaction equation
[Cl-].[CH3:2][C:3]([CH:25]=[CH:26][CH:27]=[C:28]([CH3:35])[CH2:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])=[CH:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:36][C:37](=[CH:40][CH:41]=[CH:42][CH:43]=[C:44]([CH3:47])[CH:45]=O)[CH:38]=O.CO.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.CCCCCCC>[CH3:34][C:32]([CH3:33])=[CH:31][CH2:30][CH2:29]/[C:28](/[CH3:35])=[CH:27]/[CH:26]=[CH:25]/[C:3](/[CH3:2])=[CH:4]/[CH:5]=[CH:45]/[C:44](/[CH3:47])=[CH:43]/[CH:42]=[CH:41]/[CH:40]=[C:37](\[CH3:36])/[CH:38]=[CH:5]/[CH:4]=[C:3](\[CH3:2])/[CH:25]=[CH:26]/[CH:27]=[C:28](\[CH3:35])/[CH2:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium Carbonate2×HCID 1076242,7-Dimethylocta-2,4,6-trienedialHCID 730904983,7,11-Trimethyldodeca-2,4,6,10-tetraen-1-yl-triphenylphosphonium chloride salt

Product 1

HCID 446925LycopeneYield 203.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
30 °C

Procedure

203.0 g of 3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl-triphenylphosphonium chloride salt solution (purity 58.4%, E isomer/Z isomer ratio=3.4:1) and 14.4 g of 2,7-dimethyl-2,4,6-octatriene-1,8-dial were added into 55 ml of methanol. After 316 m; of an ethyl acetate/n-heptane (w/w=1:1) solvent mixture were added, the solution mixture was heated to 30° C. Then 470.0 g of a potassium carbonate solution by dissolving 170.0 g of potassium carbonate powder in 300 g of water were added dropwise. The solution mixture was heated to 60° C. and stirred for 3 hours. Thereafter, the temperature of the solution mixture was raised to 100° C. to remove as much organic solvents as possible, then cooled to 80° C. and stirred for 16 hours. 95.9 g of lycopene wet cake were obtained by filtration. Acetone and water were added to the wet cake separately for washing and rinsing treatments. After filtration and drying, 24.6 g of synthetic lycopene crystal were obtained. HPLC analysis revealed the lycopene crystal contained 75.7% of all-E-lycopene, 19.2% of 5Z-lycopene and 3.1% of other Z-isomers. UV assay of the lycopene=99.0%.

Workup

  1. additionwere added dropwise
  2. temperatureThe solution mixture was heated to 60° C.
  3. temperatureThereafter, the temperature of the solution mixture was raised to 100° C.
  4. customto remove as much organic solvents as possible,
  5. temperaturethen cooled to 80° C.
  6. stirringstirred for 16 hours

Sources & evidence

ORD record
ord-53df77b6c13a426eb763cc80ce59a0da
Source dataset
uspto-grants-2016_09
Patent number
US09434660B2

Linked notes

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