Hydrochloric Acid → HCID 21443734, compound

HRID 328057Notes

Reaction equation

HRID 328057 reaction equation
[CH2:1]([CH:6]1[CH:10]([C:11]#N)[CH2:9][CH2:8][C:7]1=[O:13])[CH2:2][CH:3]([CH3:5])[CH3:4].[OH2:14].Cl.[CH3:16][OH:17]>>[CH2:1]([CH:6]1[C:7](=[O:13])[CH2:8][CH2:9][CH:10]1[C:11]([O:17][CH3:16])=[O:14])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 21443735HCID 21443735, compound

Product 1

HCID 21443734HCID 21443734, compound

Procedure

In a 0.5-L three-necked flask fitted with a reflux condenser, a mechanical stirrer, and a gas inlet tube, is placed a solution of 17.9 g of 2-iso-pentyl-3-cyanocyclopentanone and 2 ml of water in 200 ml of absolute methanol. Dry hydrogen chloride is passed through the refluxing solution for a period of 2 hours. The reaction mixture is maintained at reflux temperature for an additional hour. The methanol is distilled off at a reduced pressure and the residue is diluted with 300 ml of cold water. The organic layer is separated and the water phase is extracted with pentane. The combined organic layer and pentane extract are washed with sodium carbonate solution and water and dried over anhydrous sodium sulphate. The solvent is distilled off at atmospheric pressure and the residue is distilled through a short Vigreux column. Methyl 2-iso-pentyl-3-oxo-cyclopentanecarboxylate is collected at 94.5° C/0.7 mm, yield 14 g (67%), nD20 1.4561.

Workup

  1. customIn a 0.5-L three-necked flask fitted with a reflux condenser, a mechanical stirrer, and a gas inlet tube
  2. temperatureThe reaction mixture is maintained
  3. temperatureat reflux temperature for an additional hour
  4. distillationThe methanol is distilled off at a reduced pressure
  5. additionthe residue is diluted with 300 ml of cold water
  6. customThe organic layer is separated
  7. extractionthe water phase is extracted with pentane
  8. extractionThe combined organic layer and pentane extract
  9. washare washed with sodium carbonate solution and water
  10. dry with materialdried over anhydrous sodium sulphate
  11. distillationThe solvent is distilled off at atmospheric pressure
  12. distillationthe residue is distilled through a short Vigreux column
  13. customMethyl 2-iso-pentyl-3-oxo-cyclopentanecarboxylate is collected at 94.5° C/0.7 mm, yield 14 g (67%)

Sources & evidence

ORD record
ord-663d6707d8c74af1826f8a757b25d645
Source dataset
uspto-grants-1977_04
Patent number
US04016109

Reaction notes

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