Hydrochloric Acid → DL-alpha-Tocopherol
Reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH2:6][CH2:7][C:8]([CH2:14][CH2:15][CH2:16][CH:17]([CH2:19][CH2:20][CH2:21][CH:22]([CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH3:23])[CH3:18])([CH3:13])[O:9]2)=[C:4]([CH3:30])[C:3]=1[OH:31].Cl>C1(C)C=CC=CC=1.CCCCCC.[Cl-].[Cl-].[Zn+2]>[CH3:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH2:6][CH2:7][C:8]([CH2:14][CH2:15][CH2:16][CH:17]([CH2:19][CH2:20][CH2:21][CH:22]([CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH3:23])[CH3:18])([CH3:13])[O:9]2)=[C:4]([CH3:30])[C:3]=1[OH:31].[CH3:29][CH:27]([CH2:26][CH2:25][CH2:24][CH:22]([CH2:21][CH2:20][CH2:19][CH:17]([CH2:16][CH2:15][CH2:14][C:8]([OH:9])([CH:7]=[CH2:6])[CH3:13])[CH3:18])[CH3:23])[CH3:28]Participants
7
Reactant 2
Product 2
Reagents, catalysts & solvents 3
Procedure
For example, U.S. Pat. No. 4,217,285 (hereinafter '285 patent) discloses the synthesis of DL-α-tocopherol in toluene or n-hexane solvent with ZnCl2 and silica-alumina (or silica-gel) in the presence of acid, especially HCl, asserting that tocopherol can be obtained with a purity of 95 to 96% at a production yield of 99% or higher. Also, U.S. Pat. Nos. 4,634,781 and 4,639,533, both assigned to BASF, disclose processes producing for DL-α-tocopherol in which isophytol is reacted with amines such as a tridecylamine and thereafter with TMHQ in the presence of ZnCl2 and HCl, which are somewhat complicated and inefficient. In those cases, the tocopherol is described to be produced with a purity of 94 to 95% at a yield of 95 to 98%.
Workup
- customcan be obtained with a purity of 95 to 96% at a production yield of 99%
Sources & evidence
- ORD record
- ord-38f192cefce24276b202dca39813397c
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06384245B1
Reaction notes
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