1-{2-[(Prop-1-en-1-yl)oxy]ethoxy}prop-1-ene → Ethylene glycol diallyl ether

HRID 375602Notes

Reaction equation

HRID 375602 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH:9]=[CH2:10])[CH:2]=[CH2:3].CCOCC.C(OCCOC=CC)=CC>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru]Cl>[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH:9]=[CH2:10])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 539338351-{2-[(Prop-1-en-1-yl)oxy]ethoxy}prop-1-eneHCID 867492221,2-Diallyloxyethane ether

Product 1

HCID 24151Ethylene glycol diallyl ether

Reagents, catalysts & solvents 1

HCID 11007548Dichlorotris(triphenylphosphine)rutheniumCatalyst

Conditions

Temperature
120 °C

Procedure

To 46 g (0.32 mol) of 1,2-diallyloxyethane ether in a 100 mL flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was added 0.15 g (0.16 mmole) of tris(triphenylphosphine)ruthenium (II) dichloride. The reaction mixture was heated at 120° C. for two hours. Proton NMR showed that the bands assigned to the allyl groups had been completely replaced by new bands assigned to the propenyl ether groups. Gas chromatography gave three peaks which were attributed respectively to the trans,trans, trans,cis and cis,cis isomers of 1,2-dipropenoxyethane.

Workup

  1. temperaturereflux condenser and nitrogen inlet
  2. customGas chromatography gave three peaks which

Sources & evidence

ORD record
ord-c9ea3694b6484321822d9649357b584d
Source dataset
uspto-grants-1996_01
Patent number
US05486545

Reaction notes

Loading…