Hydrochloric Acid → HCID 54005510, compound

HRID 342958Notes

Reaction equation

HRID 342958 reaction equation
[Mg].[O:2]=[C:3]([CH3:12])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[N+:13]([C:16]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19])([O-:15])=[O:14].Cl>C(O)C.CCOCC.C(Cl)(Cl)(Cl)Cl>[N+:13]([C:16]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:17]=1[C:18]([CH:4]([C:3](=[O:2])[CH3:12])[C:5]([O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:6])=[O:19])([O-:15])=[O:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 15538Tert-butyl acetoacetateHCID 5462224MagnesiumHCID 143235242-Nitro-4-(trifluoromethyl)benzoyl chloride

Product 1

HCID 54005510HCID 54005510, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent3×HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of magnesium turnings (4.8 g) and carbon tetrachloride (2 ml) in pure ethanol (30 ml) was stirred and warmed gently to 50° C. until the reaction was initiated (effervescence observed). Ether (100 ml) was added cautiously with stirring. A solution of t-butyl 3-oxobutanoate (31.6 g) in ether (100 ml) was added dropwise at such a rate as to maintain the mixture at reflux. Stirring and heating at reflux was continued for 2 hours. A solution of 2-nitro-4-trifluoromethylbenzoyl chloride (50.7 g) in ether (100 ml) was added dropwise and the resultant solution was stirred and heated at reflux for 25 hours. The cooled reaction mixture was treated with hydrochloric acid (2M, 100 ml) with stirring and the two layers were separated. The organic phase was extracted with aqueous sodium hydroxide solution (2M, 2×50 ml) and water (4×50 ml). The combined aqueous layers were acidified to pH 1 and extracted with ether (2×100 ml). The combined organic layers were washed with water (50 ml), dried (anhydrous sodium sulphate) and filtered. The filtrate was evaporated to dryness to give t-butyl 2-(2-nitro-4-trifluoromethylbenzoyl)-3-oxobutanoate (62.2 g) as a crude red oil which was not further purified.

Workup

  1. stirringwith stirring
  2. temperatureto maintain the mixture
  3. temperatureat reflux
  4. stirringStirring
  5. temperatureheating
  6. temperatureat reflux
  7. temperatureheated
  8. temperatureat reflux for 25 hours
  9. customThe cooled reaction mixture
  10. stirringwith stirring
  11. customthe two layers were separated
  12. extractionThe organic phase was extracted with aqueous sodium hydroxide solution (2M, 2×50 ml) and water (4×50 ml)
  13. extractionextracted with ether (2×100 ml)
  14. washThe combined organic layers were washed with water (50 ml)
  15. dry with materialdried (anhydrous sodium sulphate)
  16. filtrationfiltered
  17. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-26853e76d2ab41b2a6bb0c2c4fe0c3a4
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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