Cyclopentanol → Cyclopentyl acrylate

HRID 2250418Notes

Reaction equation

HRID 2250418 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH:6]1([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7]1.C(N(CC)CC)C>C1COCC1>[C:1]([O:11][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7298CyclopentanolHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 85617Cyclopentyl acrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acryloyl chloride (75 mL) was added to a stirred solution of cyclopentanol (88 g, 1 mol) and triethylamine (175 mL) in dry THF (500 mL) at a rate slow enough to prevent overheating of the reaction. The reaction mixture was allowed to stand overnight, filtered through a pad of Celite, evaporated to an oil, and distilled to give cyclopentyl acrylate as a colorless liquid (bp 74-79/˜60 mm Hg). The structure of the product was confirmed by 1H NMR.

Workup

  1. customoverheating of the reaction
  2. filtrationfiltered through a pad of Celite
  3. customevaporated to an oil
  4. distillationdistilled

Sources & evidence

ORD record
ord-8a3c7cb3883d47c1b419520b625cdfd1
Source dataset
uspto-grants-2008_01
Patent number
US07317026B2

Reaction notes

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