Hydrochloric Acid → methyl (2,3,4,6-tetrahydroxyphenyl) ketone

HRID 567202Notes

Reaction equation

HRID 567202 reaction equation
O[C:2]1([OH:11])[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[CH:3]1[OH:10].[CH3:12][CH2:13][O:14]CC.C(#N)C.Cl>[Cl-].[Zn+2].[Cl-].O>[OH:11][C:2]1[C:3]([OH:10])=[C:4]([OH:9])[CH:5]=[C:6]([OH:8])[C:7]=1[C:13]([CH3:12])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 21264707HCID 21264707, compound

Product 1

HCID 11008590methyl (2,3,4,6-tetrahydroxyphenyl) ketoneYield 31.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

Under a stream of argon, 2.00 g (14.08 mmol) of 1,2,3,5-tetrahydroxyphenol (3) and 20 ml of ether were placed to form a suspension and 1.00 g (24.3 mmol, 1.73 equivalents) of acetonitrile was added to the suspension. While the resultant mixture was cooled with ice water, 0.70 g (5.14 mmol, 0.36 equivalent) of zinc chloride was added to the mixture and hydrogen chloride gas was bubbled at room temperature for four hours with stirring. The aeration of the mixture with the gas was stopped and the aerated mixture was left standing still at 4° C. for 13 hours. The ether layer was removed by decantation from the tarry precipitates consequently formed. The precipitates were stirred in an ice bath and 60 ml of water was added-to the stirred precipitates and they were heated under reflux for 4 hours. The product of the reflux, after adding a small amount of active carbon, was filtered while kept in hot. From the filtrate, yellow crystals were obtained as precipitates. By dissolving the crystals again in ether, removing the insoluble by filteration, and then concentrating the filtrate, 0.82 g (yield 31.8%) of the product (11) was obtained in the form of yellow platelike crystals.

Workup

  1. additionwas added to the suspension
  2. customwas bubbled at room temperature for four hours
  3. waitthe aerated mixture was left
  4. customThe ether layer was removed by decantation from the tarry
  5. customprecipitates consequently
  6. customformed
  7. stirringThe precipitates were stirred in an ice bath
  8. customprecipitates
  9. temperaturethey were heated
  10. temperatureunder reflux for 4 hours
  11. additionThe product of the reflux, after adding a small amount of active carbon
  12. filtrationwas filtered
  13. customFrom the filtrate, yellow crystals were obtained
  14. customas precipitates
  15. dissolutionBy dissolving the crystals again in ether
  16. customremoving the insoluble by filteration
  17. concentrationconcentrating the filtrate

Sources & evidence

ORD record
ord-5ed541502f404f3780c261bbc02e4ad8
Source dataset
uspto-grants-2001_01
Patent number
US06177474B1

Reaction notes

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