Hydrochloric Acid → HCID 20534474, compound

HRID 2399127Notes

Reaction equation

HRID 2399127 reaction equation
[CH3:1][C:2]1[C:10]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].S([O-])([O-])(=O)=O.[Ba+2].CCCCC1N=C(OCCN(C)C)C2C(=CC=CC=2)C=1.[S].[H][H].Cl>C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[C:10]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:9][CH:8]=[CH:7][C:3]=1[CH:4]=[O:5]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6857DimethisoquinHCID 24414Barium SulfateHCID 5362487SulfurHCID 20534493HCID 20534493, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20534474HCID 20534474, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
130 °C

Procedure

A mixture of 43.92 g of 2-methyl-3-(p-chlorobenzoyl)-benzoic acid chloride, 450 ml of xylene, 4.5 g of barium sulfate containing 10% palladium and 0.4 ml of a solution obtaining by refluxing 6 g of quinolein and 1 g of sulfur for 5 hours was cooled and then was diluted with 70 ml of xylene. The mixture was stirred at 130° C. while passing hydrogen therethrough for 45 minutes and the said temperature was held until evolution of hydrochloric acid ceased. An inert gas was passed therethrough at 130° C. and the mixture was then cooled to 30° C. and filtered to remove the catalyst. The solvent was distilled off and the residual oil was dissolved in isopropyl ether. Sodium bisulfite was added to the resulting solution and the mixture was stirred for 18 hours. The bisulfitic compound which precipitated was recovered by vacuum filtration, was washed and was then decomposed by stirring for 21/2 hours in the presence of dilute sulfuric acid and ether under an inert gas. The ether was decanted and the aqueous phase was extracted with ether. The combined ether phases were washed with water, dried and evaporated to dryness under reduced pressure. The residue was crystallized from isopropyl ether to obtain 24.3 g of 2-methyl-3-(p-chlorobenzoyl)-benzaldehyde melting at 68° C.

Workup

  1. customobtaining
  2. temperaturewas cooled
  3. temperatureat 130° C. and the mixture was then cooled to 30° C.
  4. filtrationfiltered
  5. customto remove the catalyst
  6. distillationThe solvent was distilled off
  7. dissolutionthe residual oil was dissolved in isopropyl ether
  8. additionSodium bisulfite was added to the resulting solution
  9. stirringthe mixture was stirred for 18 hours
  10. customThe bisulfitic compound which precipitated
  11. filtrationwas recovered by vacuum filtration
  12. washwas washed
  13. stirringby stirring for 21/2 hours in the presence of dilute sulfuric acid and ether under an inert gas
  14. customThe ether was decanted
  15. extractionthe aqueous phase was extracted with ether
  16. washThe combined ether phases were washed with water
  17. customdried
  18. customevaporated to dryness under reduced pressure
  19. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-f7f8140bfbeb4d1d9286d54d7fce860d
Source dataset
uspto-grants-1977_05
Patent number
US04027040

Reaction notes

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