Hydrochloric Acid → 2-(2,6-Dichlorophenyl)acetaldehyde

HRID 1699439Notes

Reaction equation

HRID 1699439 reaction equation
[Mg].[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:4]=1[CH2:5]Cl.CN(C)[CH:14]=[O:15].Cl>C(OCC)C>[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:4]=1[CH2:5][CH:14]=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 748322,6-Dichlorobenzyl chlorideHCID 5462224Magnesium

Product 1

HCID 122635642-(2,6-Dichlorophenyl)acetaldehydeYield 62.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 200-mL three-necked flask equipped with a thermometer, a dropping funnel, a three-way stopcock, and a mechanical stirrer was purged with nitrogen. Thereto, were added 1.85 g (76 mmol) of magnesium, and 30 mL of diethyl ether. The dropping funnel was filled with a solution of 13.5 g (69 mmol) of 2,6-dichlorobenzyl chloride (produced by Tokyo Kasei K.K.) in 40 mL of diethyl ether. The solution was added dropwise into the flask by keeping the temperature of the reaction system at about 30° C. Thereafter, the reaction mixture was aged at room temperature for 30 minutes, and cooled with ice. Thereto, 6 g (82 mmol) of N,N-dimethylformamide was added dropwise. The reaction mixture was aged at room temperature for one hour, cooled with ice, and poured into 50 mL of 3N hydrochloric acid solution. The mixture was allowed to separate into phases, and the separated matter was extracted with diethyl ether. The combined organic phase was dried over anhydrous sodium sulfate. After filtration and concentration, 5 mL of methyl t-butyl ether was added to the concentration residue, and the mixture was heated to dissolve the residue. After cooling of the solution to room temperature, the deposited crystalline matter was collected by filtration to obtain 8.1 g (43 mmol) of crystalline 2,6-dichlorophenylacetaldehyde. (Yield: 62%)

Workup

  1. customA 200-mL three-necked flask equipped with a thermometer, a dropping funnel
  2. customa three-way stopcock, and a mechanical stirrer was purged with nitrogen
  3. additionThe solution was added dropwise into the flask
  4. customat about 30° C
  5. temperaturecooled with ice
  6. waitThe reaction mixture was aged at room temperature for one hour
  7. temperaturecooled with ice
  8. customto separate into phases
  9. extractionthe separated matter was extracted with diethyl ether
  10. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  11. filtrationAfter filtration and concentration, 5 mL of methyl t-butyl ether
  12. additionwas added to the concentration residue
  13. temperaturethe mixture was heated
  14. dissolutionto dissolve the residue
  15. filtrationthe deposited crystalline matter was collected by filtration

Sources & evidence

ORD record
ord-666dfb42008a45b1883c44d1166963f0
Source dataset
uspto-grants-2002_02
Patent number
US06346621B1

Reaction notes

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