Perchloric Acid → (2,3-Dichlorophenyl)acetaldehyde

HRID 568789Notes

Reaction equation

HRID 568789 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[CH:9][O:10]C)[C:3]=1[Cl:12].Cl(O)(=O)(=O)=O>C1COCC1.O>[Cl:12][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:8][CH:9]=[O:10]

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 54186754HCID 54186754, compound

Product 1

HCID 22379768(2,3-Dichlorophenyl)acetaldehydeYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 15.0 g (0.074 mole) 1,2-dichloro-3-(2-methoxyethenyl)benzene in 150 ml of THF was added 15 ml of 35% perchloric acid in water. The reaction was refluxed for 3.5 hr then poured into ice/water. The aqueous layer was extracted two times with ether, the organics were washed with water, brine and dried (MgSO4). Evaporation of the solvent gave 13.91 g of crude 2,3-dichlorobenzeneacetaldehyde a yellow oil (99%).

Workup

  1. temperatureThe reaction was refluxed for 3.5 hr
  2. extractionThe aqueous layer was extracted two times with ether
  3. washthe organics were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9b2b2f21af104015b62024d4877aa7dd
Source dataset
uspto-grants-1988_03
Patent number
US04729994

Reaction notes

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