2-Ethylhexyl acrylate → 2-Ethylhexanoic Acid

HRID 1792154Notes

Reaction equation

HRID 1792154 reaction equation
C([O:5][CH2:6][CH:7]([CH2:12][CH3:13])[CH2:8][CH2:9][CH2:10][CH3:11])(=O)C=C.C(=O)([O-])[O-:15].[Cs+].[Cs+]>CCCCCC>[CH3:11][CH2:10][CH2:9][CH2:8][CH:7]([C:6]([OH:5])=[O:15])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 76362-Ethylhexyl acrylateHCID 10796Cesium carbonate

Product 1

HCID 86972-Ethylhexanoic AcidYield 8,029.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of TMIT (2.37 g, 15 mmol), 2-ethylhexyl acrylate (2.76 g, 15 mmol) and cesium carbonate (0.12 g, 0.38 mmol, 2.5 mole % based on acrylate) was heated in a sand bath at 100–120 ° C. for 2 h, while the progress of the reaction was being followed by IR spectroscopy. The reaction mixture was cooled to room temperature, and to the resulting thick oil was added hexane (40 mL), and the mixture was filtered to remove solid cesium carbonate. Solvent evaporation from the filtrate yielded product as a light-yellow oil (4.4 g, 86%). IR: 3323, 2961, 1733, 1481 cm−1.

Workup

  1. temperaturewas heated in a sand bath at 100–120 ° C. for 2 h, while the progress of the reaction
  2. filtrationthe mixture was filtered
  3. customto remove solid cesium carbonate
  4. customSolvent evaporation from the filtrate

Sources & evidence

ORD record
ord-052671d368d5428ab7a7b87c87dd57b7
Source dataset
uspto-grants-2006_07
Patent number
US07074937B2

Reaction notes

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