Acetone → HCID 21402622, compound

HRID 973268Notes

Reaction equation

HRID 973268 reaction equation
[OH:1][C:2]1[C:7]2[C:8](=[O:17])[CH:9]=[C:10]([C:12]([O:14]CC)=[O:13])[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.I[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:22][CH:21]([CH3:23])[CH2:20][CH2:19][O:1][C:2]1[C:7]2[C:8](=[O:17])[CH:9]=[C:10]([C:12]([OH:14])=[O:13])[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 109241-Iodo-3-methylbutaneHCID 11430Potassium CarbonateHCID 2801504ethyl 5-hydroxy-4-oxo-4H-chromene-2-carboxylate

Product 1

HCID 21402622HCID 21402622, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 23.4parts of 5-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylic acid, ethyl ester, 19.8 partsof 1-iodo-3-methylbutane, 11.65 parts of anhydrous potassium carbonate and 500 parts of acetone was refluxed for thirteen days. After cooling, the reaction mixture was filtered and the volatile components of the filtrate were removed by evaporation to give a residue which was dissolved in chloroform. The chloroform extract was washed with cold N sodium hydroxide solution, then with water and evaporated. The oily residue obtained was stirred in sodium bicarbonate solution at 100° C for 2 hour. After cooling, the solution was extracted with chloroform and the aqueous layer was separated. The aqueous extract was acidified with 2N hydrochloric acid and the mixture was extracted with chloroform. Evaporation of the chloroform gave 8.79 parts of 5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid m.p. 181°-183° C (after crystallisation from ethyl acetate/light petroleum.

Workup

  1. temperaturewas refluxed for thirteen days
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe volatile components of the filtrate were removed by evaporation
  5. customto give a residue which
  6. extractionThe chloroform extract
  7. washwas washed with cold N sodium hydroxide solution
  8. customwith water and evaporated
  9. customThe oily residue obtained
  10. temperatureAfter cooling
  11. extractionthe solution was extracted with chloroform
  12. customthe aqueous layer was separated
  13. extractionThe aqueous extract
  14. extractionthe mixture was extracted with chloroform
  15. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-8d321e5b98034f9cb7c226a7bbd72298
Source dataset
uspto-grants-1977_10
Patent number
US04055654

Reaction notes

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