Hydrochloric Acid → alpha-Tocopherol

HRID 1376922Notes

Reaction equation

HRID 1376922 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[CH:5][C:3]=1O.CCCCCC.Cl.[CH3:19][CH:20]([CH2:22][CH2:23][CH2:24][CH:25]([CH2:27][CH2:28][CH2:29][CH:30]([CH2:32][CH2:33][CH2:34][C:35]([OH:39])([CH:37]=[CH2:38])[CH3:36])[CH3:31])[CH3:26])[CH3:21]>[Cl-].[Zn+2].[Cl-].C(O)CCC>[CH3:9][C:8]1[C:7]([OH:10])=[C:6]([CH3:11])[C:5]2[CH2:38][CH2:37][C@:35]([CH2:34][CH2:33][CH2:32][C@@H:30]([CH2:29][CH2:28][CH2:27][C@@H:25]([CH2:24][CH2:23][CH2:22][CH:20]([CH3:19])[CH3:21])[CH3:26])[CH3:31])([CH3:36])[O:39][C:3]=2[C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 10453IsophytolHCID 12785Trimethylhydroquinone

Product 1

HCID 14985alpha-TocopherolYield 178.6%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 2631-ButanolSolvent

Procedure

To a mixture consisting of 69.9 g (0.260 mol) of 2,3,5-trimethylhydroquinone, 52.5 g (0.386 mol) of zinc chloride, 142.5 ml of hexane, 7.5 ml of n-butanol and 7.5 g of concentrated hydrochloric acid, 138.3 g (0.459 mol) of isophytol (purity: 98.3%) were added dropwise under stirring at 30°-40° C. over 3 hours. At the same temperature, the reaction mixture was stirred for additional 2 hours. After the reaction mixture was washed with 30 ml of water, the solvents were 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 saturated aqueous solution of NaCl dried over magnesium sulfate and then concentrated under reduced pressure, whereby 200 g of the title compound were obtained as a brown oil (yield: 98.1%, GLC purity: 97.0%).

Workup

  1. additionwere added dropwise
  2. stirringAt the same temperature, the reaction mixture was stirred for additional 2 hours
  3. washAfter the reaction mixture was washed with 30 ml of water
  4. distillationthe solvents were 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 saturated aqueous solution of NaCl dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-442a9418820d473782b2a143871cd3d1
Source dataset
uspto-grants-1997_09
Patent number
US05663376

Reaction notes

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