Carbon Dioxide → alpha-Tocopherol

HRID 259840

Reaction equation

HRID 259840 reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)O.C(=O)=O.[CH3:15][CH:16]([CH2:18][CH2:19][CH2:20][CH:21]([CH2:23][CH2:24][CH2:25][CH:26]([CH2:28][CH2:29][CH2:30][C:31]([OH:35])([CH:33]=[CH2:34])[CH3:32])[CH3:27])[CH3:22])[CH3:17]>>[CH3:10][C:4]1[C:3]([OH:11])=[C:2]([CH3:1])[C:8]2[CH2:34][CH2:33][C@:31]([CH2:30][CH2:29][CH2:28][C@@H:26]([CH2:25][CH2:24][CH2:23][C@@H:21]([CH2:20][CH2:19][CH2:18][CH:16]([CH3:15])[CH3:17])[CH3:22])[CH3:27])([CH3:32])[O:35][C:6]=2[C:5]=1[CH3:9]

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 10453IsophytolHCID 12785Trimethylhydroquinone

Product 1

HCID 14985alpha-TocopherolYield 84%

Conditions

Temperature
100 °C

Procedure

15.02 g (98.8 mmol) of trimethylhydroquinone and 10.59 g of the strongly acid ion exchanger Amberlyst A15 were placed in a 300 ml autoclave, and 116 g of CO2 were condensed in. Heating to 100° C. resulted in a pressure of 185 bar. 37.80 ml (29.48 g; 99.6 mmol) of isophytol were injected by means of an HPLC pump over the course of 1.5 hours (h) at 108° C. After stirring at 108° C. for a further 30 minutes (min), the autoclave was cooled to room temperature (RT), and the pressure was released. The ion exchanger was removed from the product by centrifuging the mixture. The 48.9 g of isolated pale yellow oil contained 83% tocopherol, which corresponds to an 84% yield of pure α-tocopherol.

Workup

  1. customcondensed in
  2. customresulted in a pressure of 185 bar
  3. customwere injected by means of an HPLC pump over the course of 1.5 hours (h) at 108° C
  4. temperaturethe autoclave was cooled to room temperature (RT)
  5. customThe ion exchanger was removed from the product by centrifuging the mixture

Sources & evidence

ORD record
ord-5ee92d81450d4ac6a59ad1a696de4d28
Source dataset
uspto-grants-1996_06
Patent number
US05523420

Linked notes

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