Water → alpha-Tocopherol

HRID 1706618Notes

Reaction equation

HRID 1706618 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][CH:7]([CH2:9][CH2:10][CH2:11][CH:12]([CH2:14][CH2:15][CH2:16][C:17]([OH:21])([CH:19]=[CH2:20])[CH3:18])[CH3:13])[CH3:8])[CH3:3].[CH3:22][C:23]1[C:24]([OH:32])=[C:25]([CH3:31])[C:26]([CH3:30])=[C:27]([CH:29]=1)O.FC(F)(F)C(O)=O.O>CCCCCC>[CH3:31][C:25]1[C:24]([OH:32])=[C:23]([CH3:22])[C:29]2[CH2:20][CH2:19][C@:17]([CH2:16][CH2:15][CH2:14][C@@H:12]([CH2:11][CH2:10][CH2:9][C@@H:7]([CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH3:8])[CH3:13])([CH3:18])[O:21][C:27]=2[C:26]=1[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 10453IsophytolHCID 12785Trimethylhydroquinone

Product 1

HCID 14985alpha-TocopherolYield 79.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Isophytol (98%, 25.5 g.) was added, dropwise, over three hours to a mixture of trimethylhydroquinone (14.5 g.), trifluoroacetic acid (65 ml.) and water (10 ml.). The product was diluted with hexane (200 ml.), washed with methanol-water (1:1, v:v)(3×100 ml.) and saturated aqueous sodium bicarbonate solution (100 ml.). A 1% by weight solution of potassium hydroxide in methanol (100 ml.) was added and the mixture was stirred at room temperature for 30 minutes. Then 2N aqueous hydrochloric acid (100 ml.) was added, the organic phase was separated, washed with saturated aqueous sodium bicarbonate solution (100 ml.) and methanol-water (1:1, v:v) (100 ml.). The hexane was removed by concentrating on a rotary evaporator and the resulting oil was flashdistilled to give α-tocopherol (29.6 g.; bp 220° C./0.1 mm.). Purity by area % glc was 100%.

Workup

  1. washwashed with methanol-water (1:1, v:v)(3×100 ml.) and saturated aqueous sodium bicarbonate solution (100 ml.)
  2. additionA 1% by weight solution of potassium hydroxide in methanol (100 ml.) was added
  3. additionThen 2N aqueous hydrochloric acid (100 ml.) was added
  4. customthe organic phase was separated
  5. washwashed with saturated aqueous sodium bicarbonate solution (100 ml.) and methanol-water (1:1, v:v) (100 ml.)
  6. customThe hexane was removed
  7. concentrationby concentrating on a rotary evaporator

Sources & evidence

ORD record
ord-6b148f894d4548a49ea255e4a9d13898
Source dataset
uspto-grants-1980_06
Patent number
US04208334

Reaction notes

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