Hydrochloric Acid → 6-Hydroxy-3-coumaranone

HRID 1613300Notes

Reaction equation

HRID 1613300 reaction equation
Cl.[C:2]1([CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[CH:4]=1)[OH:3].ClCC#N.[C:14]([O-])(=[O:16])[CH3:15].[K+]>[Cl-].[Zn+2].[Cl-].O.C(O)C.CCOCC>[OH:3][C:2]1[CH:4]=[C:5]2[C:7]([C:14](=[O:16])[CH2:15][O:6]2)=[CH:8][CH:9]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 7856ChloroacetonitrileHCID 517044Potassium Acetate

Product 1

HCID 2357176-Hydroxy-3-coumaranoneYield 54%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Hydrogen chloride gas was blown into a mixture of 150 g (1.36 moles) of resorcinol, 800 ml of dry ether, 100 g (1.32 moles) of chloroacetonitrile and 100 g (0.73 mole) of zinc chloride for about 2 hours. Crystals which precipitated were obtained by decantation. The crystals were washed with ether and 1500 ml of water was added. The mixture was refluxed for 1 hour and then cooled. The crystals were collected by filtration. Potassium acetate (130 g; 1.33 moles) and 850 ml of ethanol were added to the crystals, and the mixture was refluxed for 30 minutes. After cooling, 1500 ml of water was added, and the crystals were collected by filtration to give 107 g of the desired product (yield 54%).

Workup

  1. customCrystals which precipitated
  2. customwere obtained by decantation
  3. washThe crystals were washed with ether and 1500 ml of water
  4. additionwas added
  5. temperatureThe mixture was refluxed for 1 hour
  6. temperaturecooled
  7. filtrationThe crystals were collected by filtration
  8. temperaturethe mixture was refluxed for 30 minutes
  9. temperatureAfter cooling
  10. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-961ecc979ff7492c9eb0700e9b14d844
Source dataset
uspto-grants-1993_03
Patent number
US05192799

Reaction notes

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