CID 521661 → 2-Decyl-1,3-dioxolane

HRID 1945264Notes

Reaction equation

[C:1]([O:20][CH3:21])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]CCCCCCC.[CH3:22]CCCCCCCC=CCCCCCCCC.CC(C(O)=O)(C(O)=O)CCCCCCCC=CCCCCCCCCC>C(O)CO>[CH2:2]([CH:1]1[O:19][CH2:22][CH2:21][O:20]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

Conditions

Temperature: 120 °C

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%.

Workup

customAfter 5, 30 and 60 minutes
customafter 60 minutes

Sources & evidence

ORD record: ord-507e65493662419e8092711d47e8e586
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394996B2

Reaction notes

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