Trimethylolpropane triacrylate → 2-Ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid

HRID 884311Notes

Reaction equation

HRID 884311 reaction equation
[CH3:1][CH2:2][C:3]([CH2:16][O:17]C(C=C)=O)([CH2:10][O:11]C(C=C)=O)[CH2:4][O:5][C:6]([CH:8]=[CH2:9])=[O:7].C(S)(=S)C1C=CC=CC=1>C(Cl)Cl>[C:6]([OH:7])(=[O:5])[CH:8]=[CH2:9].[C:6]([OH:7])(=[O:5])[CH:8]=[CH2:9].[C:6]([OH:7])(=[O:5])[CH:8]=[CH2:9].[CH2:4]([C:3]([CH2:16][OH:17])([CH2:10][OH:11])[CH2:2][CH3:1])[OH:5]

Participants

4

Reactant 2

HCID 27423Trimethylolpropane triacrylateHCID 67141Benzenecarbodithioic acid

Product 1

HCID 250191762-Ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylolpropane triacrylate was purified by passing it trough a pipette packed with hydroquinone inhibitor remover (Sigma-Aldrich cat. no. 311332) and then through a pipette filled with activated alumina. TMPTA (2.03 g, 6.8 mmol) and an excess of freshly prepared dithiobenzoic acid (6.97 g, 45.3 mmol) were dissolved in 40 mL of methylene chloride. The pink solution was allowed to reflux for 6 hours. The solution was cooled to room temperature and the solvent was evaporated off under vacuum. The dark red crude material was dry mounted on a silica column and eluted with a 10% ether:hexanes solution. A purple band and then a pink band were eluted. After all the pink compound was removed, the product began to elute as an orange band. The mobile phase was changed to 50% ether:hexanes and the product was collected. The solvent was removed under vacuum to give the product as a viscous red oil. This material was stored in the freezer at 0° C.

Workup

  1. customTrimethylolpropane triacrylate was purified
  2. addition311332) and then through a pipette filled with activated alumina
  3. temperatureto reflux for 6 hours
  4. customthe solvent was evaporated off under vacuum
  5. dry with materialThe dark red crude material was dry
  6. washeluted with a 10% ether
  7. washA purple band and then a pink band were eluted
  8. customAfter all the pink compound was removed
  9. washto elute as an orange band
  10. customhexanes and the product was collected
  11. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-24d92c1624c34f1783fa246dc23a7886
Source dataset
uspto-grants-2012_08
Patent number
US08241575B2

Reaction notes

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