Diethyl Ether → HCID 21477447, compound

HRID 567201Notes

Reaction equation

HRID 567201 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].[C:12](#N)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC[O:22]CC>[Cl-].[Zn+2].[Cl-]>[C:13]1([C:12]([C:5]2[C:6]([OH:8])=[CH:7][C:2]([OH:11])=[C:3]([OH:10])[C:4]=2[OH:9])=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 7505BenzonitrileHCID 21264707HCID 21264707, compound

Product 1

HCID 21477447HCID 21477447, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Under a stream of argon, 1.30 g (9.15 mmol) of 1,2,3,5-tetrahydroxyphenol (3) was suspended in 13 ml of ether and 0.935 ml (9.15 mmol, 1.00 equivalent) of benzonitrile was added to the suspension with stirring. The resultant mixture was cooled with ice water and 0.624 g (4.57 mmol, 0.50 equivalent) of zinc chloride was added and they were stirred at room temperature for 6 hours by bubbling hydrogen chloride gas throughout. The aeration of the mixture with the gas was stopped and the mixture was left standing at 4° C. for 13 hours. From the tarry precipitates consequently formed was removed the ether layer by decantation. The precipitates were stirred in an ice bath and 39 ml of water was added and were then refluxed for 2 hours. The product of reflux was filtered while kept in hot and stand still to form red brown from the filtrate. By dissolving the crystals again in ether, filtering off insolubles from the solution, and concentrating, 0.97 g (yield 45.9%) of the product (10) was obtained in the form of orange powder crystals.

Workup

  1. additionwas added
  2. stirringthey were stirred at room temperature for 6 hours
  3. customby bubbling hydrogen chloride gas throughout
  4. waitthe mixture was left
  5. customFrom the tarry precipitates consequently
  6. customformed
  7. customwas removed the ether layer by decantation
  8. stirringThe precipitates were stirred in an ice bath
  9. addition39 ml of water was added
  10. temperaturewere then refluxed for 2 hours
  11. temperatureThe product of reflux
  12. filtrationwas filtered
  13. customto form red brown from the filtrate
  14. filtrationfiltering off insolubles from the solution
  15. concentrationconcentrating

Sources & evidence

ORD record
ord-2d1e72ba5bf94edcb7a9a9f5d9a0f025
Source dataset
uspto-grants-2001_01
Patent number
US06177474B1

Reaction notes

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