2-Ethylhexyl acrylate → 2-Ethylhexanoic Acid

HRID 1581914Notes

Reaction equation

HRID 1581914 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+]>C(#N)C>[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 399.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of TMIT (1.0 g, 6.33 mmol), 2-ethylhexyl acrylate (1.16 g, 6.33 mmol) and cesium carbonate (1.0 g, 3.3 mmol) in acetonitrile (15 mL) was stirred at room temperature for 24 h. The reaction mixture was filtered to separate solid cesium carbonate and solvent was evaporated from the filtrate to obtain the product as a colorless oil (1.9 g, 88%). IR: 3325, 2961, 1732, 1595, 1480 cm−1; 1H NMR (CDCl3, 500 MHz): δ 3.96 (overlapping d, 2 H), 3.83 (t, 1.72 H), 3.22 (t, 0.28 H), 2.82 (t, 1.72 H), 2.71 (t, 0.28 H), 1.91 (bs, 1H), 1.42 (s, 6 H), 1.40 (s, 6H), 1.35-1.20 (m, 8 H), 0.85 (overlapping t, 6 H) ppm; 13C NMR (CDCl3, 125 MHz): δ 205.8, 173.6, 171.9, 171.3, 130.2, 128.5, 88.7, 82.9, 70.35, 69.6, 67.2, 66.9, 66.8, 40.6, 38.6, 33.9, 31.4, 30.26, 30.21, 28.79, 28.71, 28.23, 25.8, 23.64, 22.83, 13.9, 10.9 ppm.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto separate solid cesium carbonate and solvent
  3. customwas evaporated from the filtrate

Sources & evidence

ORD record
ord-96f5273369d0443e8ae0f08563814f4f
Source dataset
uspto-grants-2004_05
Patent number
US06734149B2

Reaction notes

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