Hydrochloric Acid → HCID 21443734, compound

HRID 1076039Notes

Reaction equation

HRID 1076039 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. temperatureThe reaction mixture is maintained
  2. temperatureat reflux temperature for an additional hour
  3. distillationThe methanol is distilled off at a reduced pressure
  4. additionthe residue is diluted with 300 ml of cold water
  5. customThe organic layer is separated
  6. extractionthe water phase is extracted with pentane
  7. extractionThe combined organic layer and pentane extract
  8. washare washed with sodium carbonate solution and water
  9. dry with materialdried over anhydrous sodium sulphate
  10. distillationThe solvent is distilled off at atmospheric pressure
  11. distillationthe residue is distilled through a short Vigreux column
  12. 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-99b3a0ef26d64cc0902403f476b2982a
Source dataset
uspto-grants-1976_05
Patent number
US03954834

Reaction notes

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