Hydrochloric Acid → HCID 15289642, compound

HRID 1647945Notes

Reaction equation

HRID 1647945 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])=[C:8]([Cl:19])[CH:7]=1)[CH3:5].[OH-].[K+].Cl>CO>[Cl:19][C:8]1[CH:7]=[C:6]([CH:4]([CH3:5])[C:3]([OH:20])=[O:2])[CH:11]=[CH:10][C:9]=1[CH2:12][CH:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19922602HCID 19922602, compound

Product 1

HCID 15289642HCID 15289642, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 g of methyl-2-[3-chloro-4-(2-oxocyclopentane-1-yl methyl)phenyl]propionate were incorporated with 80 ml of an aqueous methanol containing 2.9 g of potassium hydroxide and then refluxed under heat for two hours. After the completion of the reaction, the reaction mixture obtained was treated to concentrate the solvent at a reduced pressure, incorporated with 50 ml of water, washed with 50 ml of ethyl acetate, after which the aqueous layer obtained was adjusted to a pH of 2 with conc. hydrochloric acid, thereafter extracted with 60 ml of ether, washed with water, dried and then freed of the solvent to obtain a residue. The thus obtained residue was distilled at a reduced pressure thereby to obtain 4.2 g (yield 88%) of oily 2-[3-chloro-4-(2-oxocyclopentane-1-yl methyl)phenyl]propionic acid.

Workup

  1. temperaturerefluxed
  2. temperatureunder heat for two hours
  3. customAfter the completion of the reaction
  4. customthe reaction mixture obtained
  5. additionwas treated
  6. concentrationto concentrate the solvent at a reduced pressure
  7. washincorporated with 50 ml of water, washed with 50 ml of ethyl acetate
  8. customafter which the aqueous layer obtained
  9. extractionextracted with 60 ml of ether
  10. washwashed with water
  11. customdried
  12. customto obtain a residue
  13. distillationThe thus obtained residue was distilled at a reduced pressure

Sources & evidence

ORD record
ord-05226784c23a41aa980331927c003f05
Source dataset
uspto-grants-1995_07
Patent number
US05434292

Reaction notes

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