Benzyl Alcohol → 4-(Benzyloxy)-2-methylidene-4-oxobutanoic acid

HRID 2061741Notes

Reaction equation

HRID 2061741 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][C:2]1=[CH2:3].[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[CH2:9]([O:16][C:5]([CH2:4][C:2](=[CH2:3])[C:1]([OH:8])=[O:7])=[O:6])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 75110Itaconic Anhydride

Product 1

HCID 113219674-(Benzyloxy)-2-methylidene-4-oxobutanoic acidYield 83.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of itaconic anhydride (33.6 g, 0.3 mol) in 100 ml of toluene is added benzyl alcohol (32.4 g, 0.3 mol). The resulting solution is heated to reflux for 3 hours. After cooling down to room temperature, hexanes (100 mL) are added to the above mixture and are continued to stir for 8 hours. A white solid is collected by filtration and washed with hexanes and dried in vacuum, giving rise to 55 g (83% yield) of the desired product: 2-(benzyloxycarbonylmethyl)acrylic acid monomer.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureto reflux for 3 hours
  3. filtrationA white solid is collected by filtration
  4. washwashed with hexanes
  5. customdried in vacuum

Sources & evidence

ORD record
ord-e3eae78941124cf28d4701c42034273b
Source dataset
uspto-grants-2012_10
Patent number
US08283413B2

Reaction notes

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