Carbon Dioxide → alpha-Tocopherol

HRID 259840

반응식

HRID 259840 반응식
[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]

참가 물질

4

반응물 3

HCID 280Carbon DioxideHCID 10453IsophytolHCID 12785Trimethylhydroquinone

생성물 1

HCID 14985alpha-Tocopherol수율 84%

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ee92d81450d4ac6a59ad1a696de4d28
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05523420

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