Acetone Cyanohydrin → 4-(2'-Nitro-4'-chlorobenzoyl)-2,2-dimethyl-2H-pyran-3,5-(4H,6H)-dione

HRID 2232013Notes

Reaction equation

HRID 2232013 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[CH3:14][C:15]1([CH3:23])[C:20](=[O:21])[CH2:19][C:18](=[O:22])[CH2:17][O:16]1.C(N(CC)CC)C.CC(C)(O)C#N>[Cl-]>[N+:1]([C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6]([CH:19]1[C:18](=[O:22])[CH2:17][O:16][C:15]([CH3:23])([CH3:14])[C:20]1=[O:21])=[O:7])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 108677844-Chloro-2-nitrobenzoyl chlorideHCID 140728872,2-dimethyl-2H-pyran-3,5(4H,6H)-dione

Product 1

HCID 140728884-(2'-Nitro-4'-chlorobenzoyl)-2,2-dimethyl-2H-pyran-3,5-(4H,6H)-dioneYield 43%

Reagents, catalysts & solvents 1

HCID 312ChlorideSolvent

Procedure

2-Nitro-4-chlorobenzoyl chloride (2.2 g, 10 mmol) and 2,2-dimethyl-2H-pyran-3,5-(4H,6H)-dione (1.4 g, 10 mmol) were dissolved in 150 milliliters (ml) chloride. Triethylamine (3 ml, 22 mmol) was added and the resulting solution stirred at room temperature for fifteen minutes. The solution was washed with dilute hydrochloric acid, 5% potassium carbonate and saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was dissolved in 10 ml acetonitrile. Triethylamine (3 ml, 22 mmol) and acetone cyanohydrin (0.2 g) were added and the mixture stirred at room temperature for 2 hours. After dilution with ether, the solution was washed with dilute hydrochloric acid and extracted with 5% potassium carbonate. The basic extract was acidified with hydrochloric acid and extracted with ether. The ether extract was washed with saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated under vacuum, yielding 1.4 g of the desired product as a viscous oil. It was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

Workup

  1. washThe solution was washed with dilute hydrochloric acid, 5% potassium carbonate and saturated sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in 10 ml acetonitrile
  5. stirringthe mixture stirred at room temperature for 2 hours
  6. washAfter dilution with ether, the solution was washed with dilute hydrochloric acid
  7. extractionextracted with 5% potassium carbonate
  8. extractionThe basic extract
  9. extractionextracted with ether
  10. extractionThe ether extract
  11. washwas washed with saturated sodium chloride
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-07cee603b254417c86f4e7b23d37c6e4
Source dataset
uspto-grants-1988_11
Patent number
US04786309

Reaction notes

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