Hydrochloric Acid → alpha-Tocopherol

HRID 1419529Notes

Reaction equation

HRID 1419529 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 101.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 2631-ButanolSolvent

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, 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-7b6e563b1a3b4bfe8ba302790eb1ad0d
Source dataset
uspto-grants-1999_03
Patent number
US05886197

Reaction notes

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