Hydrochloric Acid → alpha-Tocopherol

HRID 1419525Notes

Reaction equation

HRID 1419525 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(OCC(C)C)(=O)C>[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 102.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8038Isobutyl AcetateSolvent

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 isobutyl acetate 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 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 saturated aqueous solution of NaCl, dried over magnesium sulfate and then concentrated under reduced pressure, whereby 202.0 g of the title compound were obtained as a brown oil (yield: 99.6%, GLC purity: 97.5%).

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 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 saturated aqueous solution of NaCl, dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7379ee6c9d114069a66863e222340eea
Source dataset
uspto-grants-1999_03
Patent number
US05886197

Reaction notes

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