Itaconic acid → HCID 67973681, compound

HRID 1428993Notes

Reaction equation

HRID 1428993 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9](O)(=[O:16])[C:10]([CH2:12][C:13]([OH:15])=[O:14])=[CH2:11]>C1(C)C=CC=CC=1.O1CCOCC1>[OH:2][C:1]1[CH:3]=[C:4]2[C:6]([CH2:11][CH:10]([CH2:12][C:13]([OH:15])=[O:14])[C:9](=[O:16])[O:5]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 5054Resorcinol

Product 1

HCID 67973681HCID 67973681, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 21840791Dioxane tolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a round-bottomed flask equipped with a Dean-Stark apparatus, 10 g of resorcinol and 11.8 g of itaconic acid were dissolved in 150 ml of a toluene/dioxane mixture (volume ratio 1/1) in the presence of Amberlyst 15 resin from Aldrich. The reaction mixture was heated at 100° C. for 3 hours. After cooling, the crude reaction product was filtered and the filtrate was concentrated under vacuum. The crude product was recrystallized hot from ethyl acetate. This gave 10 g of a white powder, which corresponds to the expected product (50% yield).

Workup

  1. temperatureAfter cooling
  2. customthe crude reaction product
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe crude product was recrystallized hot from ethyl acetate

Sources & evidence

ORD record
ord-547b9582bae244f9b5e2747b309104a5
Source dataset
uspto-grants-2015_01
Patent number
US08937187B2

Reaction notes

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