Vinyl Acetate → Triethylene glycol monovinyl ether monoacetate

HRID 1792251Notes

Reaction equation

HRID 1792251 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

7

Reactant 5

HCID 7904Vinyl AcetateHCID 8172Triethylene GlycolHCID 517045Sodium AcetateHCID 575880Ethanol, 2-(2-(2-(ethenyloxy)ethoxy)ethoxy)-HCID 3033992Triethylene glycol divinyl ether

Product 1

HCID 22034547Triethylene glycol monovinyl ether monoacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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

  1. additionwere added

Sources & evidence

ORD record
ord-23d6d4ffa44348848a0b664c32a65c64
Source dataset
uspto-grants-2006_07
Patent number
US07074970B2

Reaction notes

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