Reaction #65607

ord-44849491472944fa98d8a1c6946b2944

Reaction equation

CC(C)(C)OOC(C)(C)C
di-tertbutylperoxide
C=CCO
allyl alcohol
C=CCOC(C)=O
allyl acetate
CC(C)(C)OOC(C)(C)C
di-tert-butylperoxide
C=CCO
allyl alcohol
C=CCOC(C)=O
allyl acetate
→
C=CCO.C=CCOC(C)=O
Allyl Alcohol Allyl Acetate

Reactants

CC(C)(C)OOC(C)(C)C
di-tertbutylperoxide
C=CCO
allyl alcohol
C=CCOC(C)=O
allyl acetate
CC(C)(C)OOC(C)(C)C
di-tert-butylperoxide
C=CCO
allyl alcohol
C=CCOC(C)=O
allyl acetate
—
product

Reagents

None

Conditions

Temperature
150°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureHeating
  2. 2
    Otheris isolated
  3. 3
    OtherThe yield obtained
  4. 4
    OtherGel permeation chromatography (GPC) results

Procedure

The procedure of Example 1 is generally followed. The reactor is initially charged with allyl alcohol (200 g), allyl acetate (200 g), and di-tert-butylperoxide (10 g). After heating the reactor contents to 150° C., the remaining di-tertbutylperoxide (40 g) is added to the reactor continuously over 2.5 h. Heating continues for an additional 2 h at 150° C. After vacuum stripping as described above, the product (166 g) is isolated and characterized. The yield obtained is 42% based on the weight of charged monomers. Gel permeation chromatography (GPC) results: Mw=1081, Mn=708, Mw/Mn=1.52. By 13C NMR, the product contains 57 mole % of allyl alcohol recurring units, and 43 mole % of allyl acetate recurring units.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05420216uspto-grants-1995_05