Isophytol → Alpha-Tocopherol Acetate
Reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][C:10]([CH3:12])=[O:11])[C:5]([CH3:13])=[C:4]2[CH2:14][CH2:15][C@:16]([CH2:19][CH2:20][CH2:21][C@@H:22]([CH2:24][CH2:25][CH2:26][C@@H:27]([CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH3:28])[CH3:23])([CH3:18])[O:17][C:3]=12.[CH3:35][CH:36]1[C:42]([CH3:43])=[C:41]([OH:44])[CH:40]=[C:39]([CH3:45])[C:37]1([CH2:46][C:47]([O-:49])=[O:48])[OH:38].[CH3:50][CH:51]([CH2:53][CH2:54][CH2:55][C@H:56]([CH2:58][CH2:59][CH2:60][C@H:61]([CH2:63][CH2:64][CH2:65]/[C:66](=[CH:68]/CO)/[CH3:67])[CH3:62])[CH3:57])[CH3:52].[CH3:71]C(CCCC(CCCC(CCCC(O)(C=C)C)C)C)C>>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][C:10]([CH3:12])=[O:11])[C:5]([CH3:13])=[C:4]2[CH2:14][CH2:15][C@:16]([CH2:19][CH2:20][CH2:21][C@@H:22]([CH2:24][CH2:25][CH2:26][C@@H:27]([CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH3:28])[CH3:23])([CH3:18])[O:17][C:3]=12.[CH2:43]([C:42]1[CH:36]([CH3:35])[C:37]([CH2:46][C:47]([O-:49])=[O:48])([C:39]([CH3:45])=[C:40]([CH3:71])[C:41]=1[OH:44])[OH:38])/[CH:50]=[C:51](/[CH2:53][CH2:54][CH2:55][C@@H:56]([CH2:58][CH2:59][CH2:60][C@@H:61]([CH2:63][CH2:64][CH2:65][CH:66]([CH3:68])[CH3:67])[CH3:62])[CH3:57])\[CH3:52]Participants
6
Procedure
The object is achieved by a new approach to the manufacture of α-tocopheryl acetate (TCPA). According to this approach, 2,3,6-trimethylhydroquinone-1-acetate (TMHQA) is reacted with either phytol (PH), isophytol (IP) or an (iso)phytol derivative to produce TCPA or 3-phytyl-2,5,6-trimethylhydroquinone-1-acetate (PTMHQA), whereupon the latter is submitted to ring closure to obtain TCPA.
Sources & evidence
- ORD record
- ord-b2b09272c95a412588e363efb4b58258
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07135580B2
Reaction notes
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