Alpha-Myrcene → 3,7-Dimethylene-11,15-dimethylhexadec-1-ene
Reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:10])[CH2:4][CH2:5][CH2:6][C:7](=[CH2:9])[CH3:8].Cl[CH2:12][C:13]([CH2:15][CH2:16][CH2:17][C:18](=[CH2:21])[CH:19]=[CH2:20])=[CH2:14].CC(C)([Mg]Cl)CCCCCCC>>[CH2:10]=[C:3]([CH2:4][CH2:5][CH2:6][C:7](=[CH2:8])[CH2:9][CH2:20][CH2:19][CH:18]([CH3:21])[CH2:17][CH2:16][CH2:15][CH:13]([CH3:14])[CH3:12])[CH:2]=[CH2:1]Participants
4
Procedure
Alpha-myrcene (6-methylene-2-methylocta-1,7-diene) is chlorinated to 2-chloromethyl-6-methyleneocta-1,7-diene. This is reacted with dimethyloctyl magnesium chloride to produce 3,7-dimethylene-11,15-dimethylhexadec-1-ene. This compound yields 7-methylene-3,11,15-trimethylhexadec-2-en-1-ol which, when reacted with TMHQ and hydrogenated, produces Vitamin E.
Sources & evidence
- ORD record
- ord-5e0ad57751094ae18b69b9cf2dd94c64
- Source dataset
- uspto-grants-1981_10
- Patent number
- US04293497
Reaction notes
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