DL-alpha-Tocopherol → Alpha-Tocopherol Acetate

HRID 1414007

Reaktionsgleichung

Reaktionsgleichung von HRID 1414007
C(Cl)/C=C(/CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)\C.[CH3:22][C:23]1[C:32]([CH3:33])=[C:31]2[C:26]([CH2:27][CH2:28][C:29]([CH2:35][CH2:36][CH2:37][CH:38]([CH2:40][CH2:41][CH2:42][CH:43]([CH2:45][CH2:46][CH2:47][CH:48]([CH3:50])[CH3:49])[CH3:44])[CH3:39])([CH3:34])[O:30]2)=[C:25]([CH3:51])[C:24]=1[OH:52].[C:53](OC(=O)C)(=[O:55])[CH3:54].N1C=CC(C)=CC=1>[Zn]>[CH3:33][C:32]1[C:23]([CH3:22])=[C:24]([O:52][C:53]([CH3:54])=[O:55])[C:25]([CH3:51])=[C:26]2[CH2:27][CH2:28][C@:29]([CH2:35][CH2:36][CH2:37][C@@H:38]([CH2:40][CH2:41][CH2:42][C@@H:43]([CH2:45][CH2:46][CH2:47][CH:48]([CH3:50])[CH3:49])[CH3:44])[CH3:39])([CH3:34])[O:30][C:31]=12

Komponenten

6

Edukt 4

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

Produkt 1

HCID 86472Alpha-Tocopherol AcetateAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23994ZincKatalysator

Versuchsvorschrift

2.283 g of TMHQ and 0.236 g of metallic zinc powder were suspended in 11.8 ml of ligroin in an atmosphere of nitrogen. A solution of 4.943 g of phytyl chloride [purity 95.7%] in 7.9 ml of ligroin was dripped into said suspension under agitation and refluxed for a period of 2 hours 15 minutes. The suspension was heated and subjected to reflux for another 3 hours to obtain a reaction mixture of dl-α-tocopherol. 11.5 ml of acetic anhydride and 0.218 g of γ-picoline were added to the reaction mixture, which was then refluxed for 5 hours, to obtain 7.118 g of dl-α-tocopheryl acetate which reflected a pale yellow coloring. The absorbance of this dl-α-tocopheryl acetate was determined to be E415 mμ40%EtOH =0.098. Estimation of the dl-α-tocopheryl acetate by high pressure liquid chromatography with the use of n-nonane as the standard substance indicated that its purity was 84.4% and the yield was 84.7%.

Aufarbeitung

  1. temperaturerefluxed for a period of 2 hours 15 minutes
  2. temperatureThe suspension was heated
  3. temperatureto reflux for another 3 hours
  4. customto obtain
  5. temperaturewas then refluxed for 5 hours

Quellen und Nachweise

ORD-Eintrag
ord-2c4cb1b671ae46bcb53dd9c568e4f48b
Quelldatensatz
uspto-grants-1981_02
Patentnummer
US04252726

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