2-Undecen-1-ol → Methyl Oleate
Reaction equation
[CH2:1](O)[CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7]CCCC.O[CH2:14][CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25]>>[C:24]([O:26][CH3:27])(=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]/[CH:16]=[CH:15]\[CH2:14][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:24]([OH:26])([OH:25])=[CH:23][CH2:22][CH3:21]Participants
Procedure
A mixture of 2-undecen-1-ol and methyl 11-hydroxy-9-undecenoate (0.5 ml, obtained from the cross-metathesis of methyl oleate with butenediol; composition: 8.7% methyl oleate, 13.2% 9-octadecene and 1,18-dimethyl-9-octadecenedicarboxylic acid, 61.2% alcohol cross-metathesis products, 16.9% aldehyde cross-metathesis products) and 4.5 ml of ethylene glycol are combined. Further samples are taken for GC, GC-MS and GPC. By means of a magnetic stirrer, the reaction mixture is stirred at 120° C. for 60 minutes. After 5, 30 and 60 minutes the samples for GC, GC-MS and GPC measurements are taken and the reaction is stopped. Conversion of both alcohol cross-metathesis products after 60 minutes: 90%. Total yield (over two steps) of the 2-decyl-[1,3]dioxolane (protected undecanal): 67%; total yield (over two steps) of the methyl undecanoate-11-[1,3]dioxolane (protected methyl 11-oxoundecanoate): 69%; by-products (oligomers): 5%.
Sources & evidence
- ORD record
- ord-b0a2a7369541458bbedd3e845370bf71
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394996B2
Reaction notes
Loading…