Itaconic acid → 4-Methyl hydrogen 2-methylenesuccinate

HRID 1772053Notes

Reaction equation

HRID 1772053 reaction equation
[CH2:1]=[C:2]([CH2:6][C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].[CH3:10]C1C=CC(S(N)(=O)=O)=CC=1>CO>[CH3:10][O:8][C:7](=[O:9])[CH2:6][C:2](=[CH2:1])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 6269P-Toluenesulfonamide

Product 1

HCID 817914-Methyl hydrogen 2-methylenesuccinateYield 6,533.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-methylenesuccinic acid (5.0 g, 38.4 mmol) in MeOH (200 mL) was added p-toluenesulfonamide (100 mg). The mixture was stirred at 40° C. for 2 days. The mixture was concentrated to dryness. To the residue was added DCM (200 mL). The precipitate was removed by filtration and the filtrate was concentrated to dryness to give the product as a white solid (5.5 g, 99% yield). ESI MS: m/z 145.1 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 11.17 (bs, 1H), 6.48 (s, 1H), 5.85 (s, 1H), 3.71 (s, 3H), 3.36 (s, 2H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additionTo the residue was added DCM (200 mL)
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-5677917c402941b7a29ece6933ab3b0c
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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