Sulfuric Acid → HCID 19788803, compound

HRID 1656700Notes

Reaction equation

HRID 1656700 reaction equation
[Cl:1][C:2]1([Cl:14])[CH:4]([CH3:5])[C:3]1([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]#N.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].S(=O)(=O)(O)[OH:28]>C1C=CC=CC=1.C1(C)C=CC=CC=1.CO>[Cl:1][C:2]1([Cl:14])[CH:4]([CH3:5])[C:3]1([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:6]=[O:28]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 25517Ammonium ChlorideHCID 19788804HCID 19788804, compoundHCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 19788803HCID 19788803, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

7.5 g (0.033 mol) of 2,2-dichloro-3-methyl-1-phenylcyclopropane carbonitrile were dissolved in 70 ml of dry benzene, and cooled with ice. To the resulting solution were dropwise added 25 ml of a 25% solution of diisobutylaluminium hydride in toluene in nitrogen atmosphere. The reaction mixture was stirred in nitrogen atmosphere at room temperature for 24 hours, and then further stirred at 35° C. for 5 hours. The reaction solution was cooled with ice, and admixed with 20 ml of methanol to decompose the excess diisobutylaluminium hydride. Thereafter, the reaction solution was poured into 150 ml of saturated aqueous ammonium chloride solution, and stirred for 20 minutes. 40 ml of a 10% dilute sulfuric acid were added to the reaction mixture to separate the organic phase. The aqueous phase was extracted with ether. The combined organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution and then with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The inorganic substances were filtered off, and the organic solvent was distilled off under a reduced pressure. The resultant oily residue was subjected to a distillation operation under a pressure of 0.1 mmHg (118°-119° C.) to obtain 4.5 g of 2,2-dichloro-3-methyl-1-phenylcyclopropanecarbaldehyde. Yield: 60%.

Workup

  1. temperaturecooled with ice
  2. stirringfurther stirred at 35° C. for 5 hours
  3. temperatureThe reaction solution was cooled with ice
  4. stirringstirred for 20 minutes
  5. customto separate the organic phase
  6. extractionThe aqueous phase was extracted with ether
  7. washThe combined organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution
  8. dry with materialwith a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  9. filtrationThe inorganic substances were filtered off
  10. distillationthe organic solvent was distilled off under a reduced pressure
  11. customwas subjected to a distillation operation under a pressure of 0.1 mmHg (118°-119° C.)

Sources & evidence

ORD record
ord-f54c19ffd54b47dab5fbc4e27a6340e6
Source dataset
uspto-grants-1993_10
Patent number
US05254713

Reaction notes

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