Sulfuric Acid → HCID 19788803, compound

Participants

Reaction Steps

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%.

Provenance & Evidence