Triethylamine → Isopentyl acrylate

HRID 2051521Notes

Reaction equation

HRID 2051521 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][OH:5].[C:7](Cl)(=[O:10])[CH:8]=[CH2:9].C(N(CC)CC)C>ClCCl>[C:7]([O:5][CH2:4][CH2:3][CH:2]([CH3:6])[CH3:1])(=[O:10])[CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 31260Isoamyl Alcohol

Product 1

HCID 77920Isopentyl acrylateYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-methyl butanol (2.0 g, 22.6 mmol) and acryloyl chloride (2.05 g, 22.6 mmol) in dichloromethane (5 ml) at 0° C. is added dropwise triethylamine (3.2 ml, 22.7 mmol). The solution is stirred for 30 minutes at room temperature and then concentrated to a residue. The residue is washed with hexanes (2×10 ml) and the resultant combined organics are concentrated and filtered through a plug of silica to give 3.0 g of 3-methylbutyl acrylate as an oil, 93% yield.

Workup

  1. concentrationconcentrated to a residue
  2. washThe residue is washed with hexanes (2×10 ml)
  3. concentrationthe resultant combined organics are concentrated
  4. filtrationfiltered through a plug of silica

Sources & evidence

ORD record
ord-2007a2004cb3479abe38f60a6f45bce0
Source dataset
uspto-grants-1991_05
Patent number
US05019583

Reaction notes

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