Allyl acetate → Diallyl ether

HRID 1391086Notes

Reaction equation

HRID 1391086 reaction equation
[C:1]([O:4][CH2:5][CH:6]=[CH2:7])(=O)[CH3:2].[C]=O.[CH:10]([CH2:12][C:13]([OH:15])=[O:14])=[CH2:11]>O>[CH2:1]([O:4][CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:10].[CH2:7]([O:14][C:13](=[O:15])[CH2:12][CH:10]=[CH2:11])[CH:6]=[CH2:5]

Participants

6

Reactant 3

HCID 11584Allyl acetateHCID 327433-Butenoic acidHCID 178418416HCID 178418416, compound

Product 2

HCID 11194Diallyl etherHCID 263159prop-2-en-1-yl but-3-enoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 1 liter shaking autoclave made of stainless steel was charged with 1 mol (100 grams) of allyl acetate, 0.5 gram RhCl3 . 3 H2O, 1 gram Ni(CO)4 and 18 grams of water, the autoclave was pressurized with 145 atm/g carbon monoxide and the mixture heated at 138 - 140° C. After a time of reaction of 7 hours the reaction was interrupted and the mixture analyzed. 98 grams of reaction mixture were obtained containing about 15% of vinyl acetic acid. Diallyl ether and vinyl acetic acid allyl ester were not formed. Besides acetic acid the mixture further contained the unreacted allyl acetate, small amounts of allyl alcohol, a little propionaldehyde and high boiling constituents.

Workup

  1. temperaturethe mixture heated at 138 - 140° C
  2. customAfter a time of reaction of 7 hours the reaction
  3. custom98 grams of reaction mixture
  4. customwere obtained

Sources & evidence

ORD record
ord-860e4b992e184f19bd2d17eff1e5c61d
Source dataset
uspto-grants-1979_02
Patent number
US04140865

Reaction notes

Loading…