Sulfuric Acid → HCID 54064055, compound

HRID 1608351Notes

Reaction equation

HRID 1608351 reaction equation
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6]CC)=O.[Cl:13][C:14]1[C:22]([CH3:23])=[C:21]([Cl:24])[C:20]([F:25])=[CH:19][C:15]=1C(Cl)=O.OS(O)(=O)=O>C1(C)C=CC=CC=1.O.C(O)C.C(Cl)(Cl)(Cl)Cl>[Cl:13][C:14]1[C:22]([CH3:23])=[C:21]([Cl:24])[C:20]([F:25])=[CH:19][C:15]=1[C:4]([CH2:3][C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:6]

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 5462224MagnesiumHCID 19849166HCID 19849166, compound

Product 1

HCID 54064055HCID 54064055, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 5943Carbon TetrachlorideSolvent

Procedure

3 ml of ethanol and 0.5 ml of carbon tetrachloride are added to 1.4 g of magnesium turnings. After initiation of the reaction, a mixture of 8.7 g of diethyl malonate, 6 ml of ethanol and 23 ml of toluene are added at 50° C. The mixture is warmed for 1 hour at 50°-60° C. and then cooled to -5°--10° C. A solution of 13.3 g of 2,4-dichloro-5-fluoro-3-methylbenzoyl chloride (from 2,4-dichloro-5-fluoro-3-methylbenzoic acid and thionyl chloride) in 6 ml of toluene is added dropwise at this temperature. The mixture is then allowed to come to room temperature. After standing overnight, a mixture of 24 ml of water and 4 ml of H2SO4 is added. The phases are separated, and the organic phase is washed with water, dried and concentrated. 20 ml of water and 0.1 g of p-toluenesulphonic acid are added to the oily residue. The mixture is refluxed for 4.5 hours, the phases are subsequently separated, and the organic phase is dried and concentrated in vacuo. 14.1 g of the titled compound remain as a crude oil. ##STR12##

Workup

  1. customAfter initiation of the reaction
  2. additionare added at 50° C
  3. temperatureThe mixture is warmed for 1 hour at 50°-60° C.
  4. temperaturecooled to -5°--10° C
  5. customto come to room temperature
  6. additionis added
  7. customThe phases are separated
  8. washthe organic phase is washed with water
  9. customdried
  10. concentrationconcentrated
  11. addition20 ml of water and 0.1 g of p-toluenesulphonic acid are added to the oily residue
  12. temperatureThe mixture is refluxed for 4.5 hours
  13. customthe phases are subsequently separated
  14. customthe organic phase is dried
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48c32a71fda2433396bd09fd8694ca1a
Source dataset
uspto-grants-1989_09
Patent number
US04870182

Reaction notes

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