Vinyl Acetate → Triethylene glycol monovinyl ether monoacetate

HRID 916918

Reaction equation

[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].C(O)COCCOCCO.C(OC=C)(=O)C.[CH:22]([O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32]OC=C)=[CH2:23].C(OCCOCCOCCO)=C>C1(C)C=CC=CC=1>[C:1]([O:4][CH2:32][CH2:31][O:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][O:24][CH:22]=[CH2:23])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (0.01 mmol) and sodium acetate (1.2 mmol) in toluene (2.0 ml),triethylene glycol (1 mmol) and vinyl acetate (4 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 6 hours. The reaction mixture was analyzed by gas chromatography to find that triethylene glycol divinyl ether, triethylene glycol monovinyl ether, and triethylene glycol monovinyl ether monoacetate were produced in yields of 63%, 3%, and 18%, respectively, with a conversion from triethylene glycol of 100%.

Workup

additionwere added

Sources & evidence

ORD record: ord-1d5810fe818a4bc79002725ea7c7a0d3
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271297B2

Linked notes

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