Ethyl Acetate → HCID 7172095, compound

HRID 1028440Notes

Reaction equation

HRID 1028440 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[C:9]([C:13]1[CH:14]=[CH:15][C:16]([OH:21])=[C:17]([CH:20]=1)[CH:18]=[O:19])([CH3:12])([CH3:11])[CH3:10].C(OCC)(=O)C.C([O-])(O)=O.[Na+]>C(#N)C>[C:9]([C:13]1[CH:14]=[C:15]([N+:7]([O-:8])=[O:6])[C:16]([OH:21])=[C:17]([CH:20]=1)[CH:18]=[O:19])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 14750905-tert-ButylsalicylaldehydeHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 7172095HCID 7172095, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-15 °C

Procedure

At −30° C. 4.84 g nitroniumtetrafluoroborate are added to a solution of 5.00 g 5-tert-butyl-2-hydroxy-benzaldehyde in 200 ml acetonitrile. The solution is heated to −15° C. within 1 h and then combined with ethyl acetate and saturated aqueous NaHCO3 solution. The resulting mixture is extracted with ethyl acetate, and the combined extracts are washed with saturated aqueous saline solution, dried (MgSO4) and evaporated down. The residue is taken up in 2 ml of water and 40 ml concentrated acetic acid, and the resulting mixture is refluxed for 2 h. The cooled solution is poured into ice-cold water, and the precipitate formed is filtered off and dissolved in ethyl acetate. The organic solution is dried (MgSO4) and evaporated down. The oil remaining rapidly solidifies.

Workup

  1. customAt −30° C
  2. extractionThe resulting mixture is extracted with ethyl acetate
  3. washthe combined extracts are washed with saturated aqueous saline solution
  4. dry with materialdried (MgSO4)
  5. customevaporated down
  6. temperature40 ml concentrated acetic acid, and the resulting mixture is refluxed for 2 h
  7. additionThe cooled solution is poured into ice-cold water
  8. customthe precipitate formed
  9. filtrationis filtered off
  10. dissolutiondissolved in ethyl acetate
  11. dry with materialThe organic solution is dried (MgSO4)
  12. customevaporated down

Sources & evidence

ORD record
ord-547352db580d4dd7bca90579c2846a73
Source dataset
uspto-grants-2014_05
Patent number
US08735579B2

Reaction notes

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