Hydrochloric Acid → HCID 18471013, compound

HRID 2228659Notes

Reaction equation

HRID 2228659 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].Cl[CH2:13][CH2:14][C:15]([OH:17])=[O:16].Cl.S(=O)(=O)(O)O.[CH2:24](O)[CH3:25]>[OH-].[K+]>[O:11]=[C:6]1[C:7]2[C:3](=[C:2]([O:1][CH2:13][CH2:14][C:15]([O:17][CH2:24][CH3:25])=[O:16])[CH:10]=[CH:9][CH:8]=2)[CH2:4][CH2:5]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1118Sulfuric AcidHCID 78993-Chloropropionic acidHCID 5905474-Hydroxy-1-indanone2×

Product 1

HCID 18471013HCID 18471013, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

To a solution of 2,3-dihydro-4-hydroxy-1H-inden-1-one (18.0 g, 121 mmol) in 30% aqueous potassium hydroxide solution (60 mL) was added 3-chloropropionic acid (18 g, 166 mmol) at room temperature and the mixture was refluxed for 1 hour. After cooling, 1N-hydrochloric acid was added and the precipitate (10.0 g) comprised of unreacted 2,3-dihydro-4-hydroxy-1H-inden-1-one was separated by filtration. The filtrate was extracted with 2 portions of ethyl acetate and the pooled extract was washed with water, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure to provide crude crystals (6.20 g) of 3-[(2,3-dihydro-1-oxo-1H-inden-4-yl)oxy]propionic acid. This crystal crop was dissolved in ethanol (40 mL) followed by addition of concentrated sulfuric acid (1.0 mL) at room temperature and the mixture was refluxed for 1 hour. After cooling, the reaction mixture was extracted with 2 portions of ethyl acetate and the pooled organic solution was washed with saturated aqueous sodium hydrogen carbonate solution, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was crystallized from hexane-diisopropyl ether to provide 6.50 g of the title compound. Yield 22%.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. customwas separated by filtration
  4. extractionThe filtrate was extracted with 2 portions of ethyl acetate
  5. extractionthe pooled extract
  6. washwas washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customto provide crude crystals (6.20 g) of 3-[(2,3-dihydro-1-oxo-1H-inden-4-yl)oxy]propionic acid
  11. temperaturethe mixture was refluxed for 1 hour
  12. temperatureAfter cooling
  13. extractionthe reaction mixture was extracted with 2 portions of ethyl acetate
  14. washthe pooled organic solution was washed with saturated aqueous sodium hydrogen carbonate solution
  15. dry with materialdried over MgSO4
  16. filtrationfiltered
  17. concentrationThe filtrate was concentrated under reduced pressure
  18. customthe residue was crystallized from hexane-diisopropyl ether

Sources & evidence

ORD record
ord-a633245bc3434e259ea4226560e68261
Source dataset
uspto-grants-2002_07
Patent number
US06417213B2

Reaction notes

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