Hydrochloric Acid → HCID 53957141, compound

HRID 1701353Notes

Reaction equation

HRID 1701353 reaction equation
[C:1]([C:3]1[C:4]([CH3:12])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7])#[N:2].[ClH:13]>C1C=CC=CC=1.O.[Cd].ClC1C=CC=CC=1.ClC1C=CC=CC=1>[Cl:13][C:3]1[CH:4]=[CH:5][C:9]([C:6]([C:5]2[C:4]([CH3:12])=[C:3]([CH:11]=[CH:10][CH:9]=2)[C:1]#[N:2])=[O:7])=[CH:10][CH:11]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 20347860HCID 20347860, compound

Product 1

HCID 53957141HCID 53957141, compound

Reagents, catalysts & solvents 3

HCID 86736859HCID 86736859, compoundCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

The said benzene solution was cooled to 5° C. and then a solution of 27.4 g of 3-cyano-2-methyl-benzoyl chloride in 85 cc of benzene was added thereto. The mixture was allowed to return to room temperature and was stirred overnight. The mixture was refluxed for 31/2 hours and after cooling, the mixture was added to a solution of 30 cc of hydrochloric acid in 600 cc of water. The mixture was extracted with ether and the combined ether phases were washed successively with 1 N hydrochloric acid, water, 1 N sodium hydroxide and water until the wash waters were neutral. The organic phase was dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was empasted with 40 cc of petroleum ether, vacuum filtered, washed with petroleum ether and dried at room temperature under reduced pressure to obtain 30.6 g of 3-p-chlorobenzoyl-2-methyl-benzonitrile. For analysis, the product was crystallized from methanol and melted at 84° C. The compound occurred in the form of beige crystals soluble in methylene chloride and chloroform.

Workup

  1. customto return to room temperature
  2. temperatureThe mixture was refluxed for 31/2 hours
  3. temperatureafter cooling
  4. extractionThe mixture was extracted with ether
  5. washthe combined ether phases were washed successively with 1 N hydrochloric acid, water, 1 N sodium hydroxide and water until the wash waters
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. filtrationfiltered
  9. washwashed with petroleum ether
  10. customdried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-6b10da51b44b4d0cb1cc547d8d7b63bf
Source dataset
uspto-grants-1980_03
Patent number
US04192890

Reaction notes

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