Water → 5-(2-Oxocyclopentyl)pentyl acetate

HRID 2051782Notes

Reaction equation

HRID 2051782 reaction equation
C(OC([C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:20])[CH3:19])[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])=O)C.O.S(=O)(=O)(O)O>C(O)(=O)C>[C:18]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 54157506Ethyl 1-[5-(acetyloxy)pentyl]-2-oxocyclopentane-1-carboxylate

Product 1

HCID 131315305-(2-Oxocyclopentyl)pentyl acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

300 g of 1-(5-acetoxypentyl)-2-oxo-cyclopentane-carboxylic acid ethyl ester were refluxed for 5 hours in 1.5 l of acetic acid, 600 ml of water and 300 g of sulfuric acid. Subsequently, the solution was concentrated under reduced pressure, 1liter of semi-saturated sodium chloride solution was added, and the solution was extracted with acetic acid ethyl ester. The organic phase was washed with 500 ml of saturated sodium chloride solution and dried over sodium sulfate. 50 ml of acetic anhydride were added, and the whole was refluxed for 4 hours. The solvent was distilled off under reduced pressure and the residue was subjected to fractional distillation under reduced pressure in a column having a height of 30 cm.

Workup

  1. concentrationSubsequently, the solution was concentrated under reduced pressure, 1liter of semi-saturated sodium chloride solution
  2. additionwas added
  3. extractionthe solution was extracted with acetic acid ethyl ester
  4. washThe organic phase was washed with 500 ml of saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. addition50 ml of acetic anhydride were added
  7. temperaturethe whole was refluxed for 4 hours
  8. distillationThe solvent was distilled off under reduced pressure
  9. distillationthe residue was subjected to fractional distillation under reduced pressure in a column

Sources & evidence

ORD record
ord-789f46305dab4450afeb5338d9859e15
Source dataset
uspto-grants-1980_01
Patent number
US04182773

Reaction notes

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