Itaconic acid → HCID 86617348, compound

HRID 1044472Notes

Reaction equation

HRID 1044472 reaction equation
[CH3:1][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([CH2:31][OH:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C@@H:16]([OH:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:3].[C:33]([OH:38])(=[O:37])[C@H:34]([CH3:36])[OH:35].[C:39]([OH:47])(=[O:46])[C:40]([CH2:42][C:43]([OH:45])=[O:44])=[CH2:41]>O>[C:33]([OH:38])(=[O:37])[CH:34]([CH3:36])[OH:35].[C:39]([OH:47])(=[O:46])[C:40]([CH2:42][C:43]([OH:45])=[O:44])=[CH2:41].[CH3:3][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([CH2:31][OH:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C@@H:16]([OH:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:1]

Participants

5

Reactant 3

HCID 811Itaconic acidHCID 72326Betulin2×HCID 107689L-Lactic Acid

Product 1

HCID 86617348HCID 86617348, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Polymerisation was performed in the same principle as in Example 9, but the betulin was added to the reaction mixture in three portions during first two hours. The amounts of the ingredients were following: 85.2 g of L-lactic acid (89 mole-%), 7.4 g of itaconic acid (5.5 mole-%), 25 g of betulin (5.5 mole-%) and 0.0375 g of tin(II)octoate. Total polymerisation time was 14 hours. The product was hard, brittle, shiny, orange mass, which was water resistant. Synthesis product was observed to crosslink with end-functionalisation (Example 11) by radicals.

Workup

  1. customPolymerisation
  2. customSynthesis product

Sources & evidence

ORD record
ord-c1e3f2302f154f4ba5c9f82451c19642
Source dataset
uspto-grants-2013_10
Patent number
US08563664B2

Reaction notes

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