DL-alpha-Tocopherol → Alpha-Tocopherol Acetate

HRID 1414009

Reaction equation

HRID 1414009 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](OCC)(=[O:56])[CH3:55]>[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

6

Reactant 4

HCID 2116DL-alpha-Tocopherol3×HCID 8857Ethyl Acetate2×HCID 5352426Tin atom3×HCID 11130851Phytyl chloride2×

Product 1

HCID 86472Alpha-Tocopherol AcetateYield 84.5%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

3.040 g of TMHQ, 0.484 g of metallic tin powder and 0.079 g of zinc chloride were suspended in 15 ml of ethyl acetate in an atmosphere of nitrogen. A solution of 7.975 g of phytyl chloride in 10 ml of ethyl acetate was dripped into said suspension over a period of 3 hours under heating and reflux. About 0.1 g metallic tin powder was added eight times, same amount per addition, in order to maintain said tin continuously suspended in the suspension. After addition of the phytyl chloride, the reaction mixture was subjected to heating and reflux for another 3 hours to obtain a reaction mixture of dl-α-tocopherol. The obtained dl-α-tocopherol was acetylated in the same manner as described in Comparative Example 1 without isolating said dl-α-tocopherol to obtain 10.454 of dl-α-tocopheryl acetate. The absorbance of this crude dl-α-tocopheryl acetate was measured: E415 mμ40%EtOH =0.145. Estimation of the crude dl-α-tocopheryl acetate by liquid chromatography indicated that its purity was 76.3% and the yield was 84.5%.

Workup

  1. customof 3 hours
  2. temperatureunder heating
  3. temperaturereflux
  4. additionper addition
  5. temperaturein order to maintain
  6. temperatureto heating
  7. temperaturereflux for another 3 hours
  8. customto obtain
  9. customwithout isolating

Sources & evidence

ORD record
ord-9574e8701ab949889ef043e5c7e99d92
Source dataset
uspto-grants-1981_02
Patent number
US04252726

Linked notes

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