Hydrochloric Acid → HCID 21541490, compound

HRID 1076013Notes

Reaction equation

HRID 1076013 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:12](=[O:19])[CH2:13][CH:14]([OH:18])[C:15]=1[C:16]#[N:17])([O:3][CH3:4])=[O:2].Cl>[Zn].C(O)(=O)C>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH:15]([C:16]#[N:17])[CH:14]([OH:18])[CH2:13][C:12]1=[O:19])([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21541510HCID 21541510, compound

Product 1

HCID 21541490HCID 21541490, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Into a mixture of 7 g of 2-(6'-carbomethoxyhexyl)-3-cyano-4-hydroxy-2-cyclopenten-1-one, 52.5 ml of acetic acid and 55 ml of 0.5 N hydrochloric acid was added 15 g of zinc powder. After the addition the reaction mixture was stirred for 3 hours under cooling. Thereafter, the zinc powder was removed by filtration, and the filtrate was diluted with water and extracted with ether. The ether extract was washed with a diluted aqueous sodium bicarbonate solution and with water and then dried. The solvent was distilled off to afford 4.5 g of 2-(6'-carbomethoxyhexyl)-3-cyano-4-hydroxy-cyclopentanone.

Workup

  1. additionAfter the addition the reaction mixture
  2. temperatureunder cooling
  3. customThereafter, the zinc powder was removed by filtration
  4. additionthe filtrate was diluted with water
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washwas washed with a diluted aqueous sodium bicarbonate solution and with water
  8. customdried
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-a4da38e28eef44e5b7f9a511cb9e1918
Source dataset
uspto-grants-1976_05
Patent number
US03954811

Reaction notes

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