Hydrochloric Acid → HCID 20331380, compound

HRID 2057587Notes

Reaction equation

HRID 2057587 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8][CH2:9][CH3:10])=O.Cl.O1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=O)[CH:18]=[CH:17]1>C(O)C>[O:1]=[C:2]1[C:10]2[CH:21]=[C:22]3[CH2:23][CH2:24][CH2:25][CH2:20][CH2:19][C:18]3=[CH:17][C:9]=2[O:8][C:6]([C:5]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7268Diethyl OxalateHCID 10286ChromoneHCID 2723922Sodium ethoxide

Product 1

HCID 20331380HCID 20331380, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of the product from step (b) (10 gm) in ethanol (50 ml) was added to sodium ethoxide solution (prepared by dissolving sodium (5.75 gm) in ethanol (150 ml)) and stirred at room temperature for ten minutes. Diethyl oxalate (17.5 gm) in ethanol (30 ml) was added dropwise and the reaction mixture was refluxed for 90 minutes, cooled, poured into dilute hydrochloric acid and extracted with chloroform. Removal of the chloroform in vacuo yielded a brown oil which was refluxed with ethanol (150 ml) containing conc. hydrochloric acid (80 ml) for five hours. The bulk of the solvent was removed in vacuo and the residues were poured into water and extracted with ethyl acetate. After washing with brine and water the ethyl acetate was removed in vacuo yielding a brown oil which was found to contain the chromone ester and the chromone acid. Trituration of the oil with 40°/60° C. petroleum ether yielded the title compound, a fawn coloured solid which was crystallised from aqueous ethanol. Wt 0.34 gm. Mpt. 74°-75 ° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 90 minutes
  2. temperaturecooled
  3. extractionextracted with chloroform
  4. customRemoval of the chloroform in vacuo
  5. customyielded a brown oil which
  6. customThe bulk of the solvent was removed in vacuo
  7. additionthe residues were poured into water
  8. extractionextracted with ethyl acetate
  9. washAfter washing with brine and water the ethyl acetate
  10. customwas removed in vacuo
  11. customyielding a brown oil which

Sources & evidence

ORD record
ord-01c99612eb82469c8080c573b07b25da
Source dataset
uspto-grants-1980_07
Patent number
US04211788

Reaction notes

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