Acetic Anhydride → Alpha-Tocopherol Acetate

HRID 1979090Notes

Reaction equation

HRID 1979090 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[CH3:5][C:6]1[C:7](O)=[C:8]([CH3:14])[C:9]([CH3:13])=[C:10]([CH:12]=1)O.[CH3:16][CH:17]([CH2:19][CH2:20][CH2:21][CH:22]([CH2:24][CH2:25][CH2:26][CH:27]([CH2:29][CH2:30][CH2:31][C:32]([OH:36])([CH:34]=[CH2:35])[CH3:33])[CH3:28])[CH3:23])[CH3:18].C(OC(=O)C)(=O)C>>[CH3:13][C:9]1[C:8]([CH3:14])=[C:7]([O:3][C:1]([CH3:2])=[O:4])[C:6]([CH3:5])=[C:12]2[CH2:35][CH2:34][C@:32]([CH2:31][CH2:30][CH2:29][C@@H:27]([CH2:26][CH2:25][CH2:24][C@@H:22]([CH2:21][CH2:20][CH2:19][CH:17]([CH3:16])[CH3:18])[CH3:23])[CH3:28])([CH3:33])[O:36][C:10]=12

Participants

4

Reactant 3

HCID 7918Acetic Anhydride2×HCID 10453IsophytolHCID 87768587HCID 87768587, compound

Product 1

HCID 86472Alpha-Tocopherol Acetate

Procedure

The condensation of trimethylhydroquinone monoacetate (TMHQ-MA) with isophytol is described in DE-OS 2 160 103 (=U.S. Pat. No. 3,789,086). With the use of Fe (II) Cl2 and hydrochloric acid and simultaneous removal of the water of reaction, only small quantities of α-tocopherol acetate are obtained and it is necessary to acetylate subsequently with amine catalysis and addition of hyperstoichiometric quantities of acetic anhydride. The yields are unsatisfactory, the two-step procedure is expensive and the necessity of reacting with hyperstoichiometric quantities of acetic anhydride to obtain vitamin E acetate entails a high consumption of chemicals. The working-up of the catalyst phase obtained after the reaction is not dealt with.

Workup

  1. customWith the use of Fe (II) Cl2 and hydrochloric acid and simultaneous removal of the water of reaction, only small quantities of α-tocopherol acetate
  2. customare obtained

Sources & evidence

ORD record
ord-382d49b4f86e49fb9f95fe63dce63e04
Source dataset
uspto-grants-2001_05
Patent number
US06239294B1

Reaction notes

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