Hydrochloric Acid → alpha-Tocopherol

HRID 376503Notes

Reaction equation

HRID 376503 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[CH:5][C:3]=1O.Cl.[CH3:13][CH:14]([CH2:16][CH2:17][CH2:18][CH:19]([CH2:21][CH2:22][CH2:23][CH:24]([CH2:26][CH2:27][CH2:28][C:29]([OH:33])([CH:31]=[CH2:32])[CH3:30])[CH3:25])[CH3:20])[CH3:15]>[Cl-].[Zn+2].[Cl-].C(=O)(OCC)OCC>[CH3:9][C:8]1[C:7]([OH:10])=[C:6]([CH3:11])[C:5]2[CH2:32][CH2:31][C@:29]([CH2:28][CH2:27][CH2:26][C@@H:24]([CH2:23][CH2:22][CH2:21][C@@H:19]([CH2:18][CH2:17][CH2:16][CH:14]([CH3:13])[CH3:15])[CH3:20])[CH3:25])([CH3:30])[O:33][C:3]=2[C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10453IsophytolHCID 12785Trimethylhydroquinone

Product 1

HCID 14985alpha-TocopherolYield 101.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7766Diethyl CarbonateSolvent

Conditions

Temperature
35 °C

Procedure

To a mixture consisting of 69.9 g (0.460 mol) of 2,3,5-trimethylhydroquinone, 52.5 g (0.386 mol) of zinc chloride, 150 ml of diethyl carbonate and 7.5 g of concentrated hydrochloric acid, 138.3 g (0.459 mol) of isophytol (purity: 98.3%) was added dropwise under stirring at 30-40° C. over 3 hours. At the same temperature, the reaction mixture was stirred for an additional 2 hours. After the reaction mixture was washed with 30 ml of water, the solvent was distilled off. Toluene (300 ml) was added to the residue to dissolve the same. The resulting solution was washed successively with water, alkaline water and a saturate aqueous solution of NaCl, dried over magnesium sulfate and then concentrated under reduced pressure, whereby 201.2 g of the title compound was obtained as a brown oil (yield: 99.2%), GLC purity: 97.5%).

Workup

  1. additionwas added dropwise
  2. stirringAt the same temperature, the reaction mixture was stirred for an additional 2 hours
  3. washAfter the reaction mixture was washed with 30 ml of water
  4. distillationthe solvent was distilled off
  5. additionToluene (300 ml) was added to the residue
  6. dissolutionto dissolve the same
  7. washThe resulting solution was washed successively with water
  8. dry with materialalkaline water and a saturate aqueous solution of NaCl, dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-198fa4d8df0f4f8ea6df5d12283d4d4f
Source dataset
uspto-grants-2000_02
Patent number
US06020505

Reaction notes

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