Ethanol → Ethyl 2-cyclopentylacetate

HRID 1668813Notes

Reaction equation

HRID 1668813 reaction equation
S(=O)(=O)(O)O.[CH:6]1([CH2:11][C:12]([OH:14])=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:15][CH2:16]O>>[CH2:15]([O:13][C:12](=[O:14])[CH2:11][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 71606Cyclopentylacetic acid

Product 1

HCID 247667Ethyl 2-cyclopentylacetate

Procedure

Concentrated sulfuric acid (1 mL) was added to a solution of cyclopentylacetic acid (5.8 mL, 46 mmol) in anhydrous EtOH (15 mL) and heated to reflux for 3 hours. Thereafter, volatiles were removed under reduced pressure and the residue was diluted with water and ethyl acetate. The organic layer was separated, washed with 5% sodium bicarbonate, brine, dried over Na2SO4, and filtered. After evaporation of solvent under reduced pressure, a syrupy cyclopentylacetic acid ethyl ester was obtained and used in the next step without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customThereafter, volatiles were removed under reduced pressure
  4. additionthe residue was diluted with water and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with 5% sodium bicarbonate, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customAfter evaporation of solvent under reduced pressure

Sources & evidence

ORD record
ord-1a4fe67562bb462eac2d7b0864f187aa
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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