DL-alpha-Tocopherol → Alpha-Tocopherol Acetate

HRID 1414010

Reaction equation

HRID 1414010 reaction equation
[Sn].C(Cl)/C=C(/CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)\C.[CH3:23][C:24]1[C:33]([CH3:34])=[C:32]2[C:27]([CH2:28][CH2:29][C:30]([CH2:36][CH2:37][CH2:38][CH:39]([CH2:41][CH2:42][CH2:43][CH:44]([CH2:46][CH2:47][CH2:48][CH:49]([CH3:51])[CH3:50])[CH3:45])[CH3:40])([CH3:35])[O:31]2)=[C:26]([CH3:52])[C:25]=1[OH:53].[C:54](OC(=O)C)(=[O:56])[CH3:55].N1C=CC(C)=CC=1>[Cl-].[Zn+2].[Cl-]>[CH3:34][C:33]1[C:24]([CH3:23])=[C:25]([O:53][C:54]([CH3:55])=[O:56])[C:26]([CH3:52])=[C:27]2[CH2:28][CH2:29][C@:30]([CH2:36][CH2:37][CH2:38][C@@H:39]([CH2:41][CH2:42][CH2:43][C@@H:44]([CH2:46][CH2:47][CH2:48][CH:49]([CH3:51])[CH3:50])[CH3:45])[CH3:40])([CH3:35])[O:31][C:32]=12

Participants

7

Reactant 5

HCID 2116DL-alpha-TocopherolHCID 7918Acetic AnhydrideHCID 79634-MethylpyridineHCID 5352426Tin atomHCID 11130851Phytyl chloride

Product 1

HCID 86472Alpha-Tocopherol AcetateYield 95%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

2.279 of TMHQ, 0.368 g of metallic tin powder and 0.041 g of zinc chloride were suspended in 15 ml of trichlene in an atmosphere of nitrogen. A solution of 4.939 g of phytyl chloride in 10 ml of trichlene was dripped into said suspension over a period of 2.5 hours under agitation and reflux. The reaction mixture was subjected to reflux under agitation for another 2 hours to obtain a reaction mixture containing dl-α-tocopherol which was substantially achromatic. To the reaction mixture was added 13.0 ml of acetic anhydride and 0.219 g of γ-picoline and the mixture was subjected to reflux for 2.5 hours. The lower boiling fractions were distilled off from the reaction mixture under reduced pressure. The reaction mixture was extracted with n-hexane in an amount of 50 ml, and the extract was washed 4 times with an aqueous solution of 2% sodium hydrosulfite, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 7.167 g of dl-α-tocopheryl acetate which was a substantially achromatic viscous liquid. The absorbance of this crude dl-α-tocopheryl acetate was measured: E415 mμ40%EtOH =0.041. Estimation of this crude dl-α-tocopheryl acetate by liquid chromatography with the use of n-nonane as the standard indicated that its purity was 93.8% and the yield was 95.0%.

Workup

  1. customof 2.5 hours
  2. temperaturereflux
  3. temperatureto reflux under agitation for another 2 hours
  4. customto obtain a reaction mixture
  5. temperatureto reflux for 2.5 hours
  6. distillationThe lower boiling fractions were distilled off from the reaction mixture under reduced pressure
  7. extractionThe reaction mixture was extracted with n-hexane in an amount of 50 ml
  8. washthe extract was washed 4 times with an aqueous solution of 2% sodium hydrosulfite
  9. dry with materialdried with anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a42c00f97ca4f31b9466d5e3c565e08
Source dataset
uspto-grants-1981_02
Patent number
US04252726

Linked notes

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