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Allyl Alcohol → Allyl Alcohol Allyl Acetate

HRID 37329
Notes
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Reaction equation

HRID 37329 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].[C:5]([O:8][CH2:9][CH:10]=[CH2:11])(=[O:7])[CH3:6].C(OOC(C)(C)C)(C)(C)C>>[CH2:1]([OH:4])[CH:2]=[CH2:3].[C:5]([O:8][CH2:9][CH:10]=[CH2:11])(=[O:7])[CH3:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 7858Allyl Alcohol2×HCID 8033Di-tert-butyl peroxide2×HCID 11584Allyl acetate2×

Product 1

HCID 131719011Allyl Alcohol Allyl Acetate

Conditions

Temperature
150 °C

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.

Workup

  1. temperatureHeating
  2. customis isolated
  3. customThe yield obtained
  4. customGel permeation chromatography (GPC) results

Sources & evidence

ORD record
ord-44849491472944fa98d8a1c6946b2944
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05420216

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes