Itaconic acid → 4-Methyl hydrogen 2-methylenesuccinate

HRID 1387701

Reaction equation

HRID 1387701 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=[O:6])=[CH2:3].[C:10](Cl)(=O)C1C=CC=CC=1>CO>[CH3:10][O:6][C:5]([CH2:4][C:2]([C:1]([OH:9])=[O:8])=[CH2:3])=[O:7]

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 7412Benzoyl chloride

Product 1

HCID 817914-Methyl hydrogen 2-methylenesuccinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (100 ml) solution of itaconic acid (100 g), benzoyl chloride (4 ml) was added dropwise under stirring. The reaction solution was stirred at 60-70° C. for 20 minutes and then concentrated under reduced pressure. The resulting solid was recrystallized from a mixed solution of benzene and petroleum ether to obtain 4-methyl itaconate (93 g, melting point: 65-67° C.).

Workup

  1. stirringThe reaction solution was stirred at 60-70° C. for 20 minutes
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting solid was recrystallized from a mixed solution of benzene and petroleum ether

Sources & evidence

ORD record
ord-8b1844667bde477aa74942da04cd3b90
Source dataset
uspto-grants-2001_07
Patent number
US06268511B1

Linked notes

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