Hydrochloric Acid → HCID 14958195, compound

HRID 1079305Notes

Reaction equation

HRID 1079305 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:11])[CH2:9][CH3:10].[C:12](OCC)(=O)[C:13]([O:15]CC)=[O:14].[O-]CC.[Na+].Cl>C(O)C.C(O)(=O)C.O>[CH3:10][C:9]1[C:8](=[O:11])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:1][C:12]=1[C:13]([OH:15])=[O:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 691332'-HydroxypropiophenoneHCID 2723922Sodium ethoxide

Product 1

HCID 14958195HCID 14958195, compoundYield 13%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2'-Hydroxypropiophenone (15.02 g) and diethyl oxalate (17.54 g) were added to a solution of sodium ethoxide in ethanol (prepared from 6.90 g of sodium and 200 ml of ethanol), and the mixture was heated for 2.5 hours while refluxing. The mixture was cooled, poured over 2N HCl (320 ml) and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:3, v/v) to yield an oily substance (4.26 g). This oily substance was dissolved in acetic acid-concentrated hydrochloric acid (1:1, 30 ml) and heated for 1 hour while refluxing. After cooling, the reaction mixture was poured over water (150 ml) and stirred at room temperature for 10 minutes. The separated crystals were collected by filtration to yield 3-methyl-4-oxo-4H-1-benzopyran-2-carboxylic acid (2.62 g, 13%), which was then recrystallized from ethanol to yield colorless prisms having a melting point of 192° to 193° C.

Workup

  1. temperaturethe mixture was heated for 2.5 hours
  2. temperaturewhile refluxing
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationafter which the solvent was distilled off
  8. washeluted with ethyl acetate-hexane (1:3
  9. customv/v) to yield an oily substance (4.26 g)
  10. temperatureheated for 1 hour
  11. temperaturewhile refluxing
  12. temperatureAfter cooling
  13. filtrationThe separated crystals were collected by filtration

Sources & evidence

ORD record
ord-5d60ff39d7064c99a7072791b8e9a9cb
Source dataset
uspto-grants-1996_12
Patent number
US05580863

Reaction notes

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