Hydrochloric Acid → (2-Chloro-4-nitrophenyl)acetaldehyde

HRID 735125Notes

Reaction equation

HRID 735125 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1/[CH:12]=[CH:13]/N(C)C.C([OH:19])C>>[Cl:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH2:12][CH:13]=[O:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 11310699(E)-2-(2-chloro-4-nitrophenyl)-N,N-dimethylethenamine

Product 1

HCID 54570839(2-Chloro-4-nitrophenyl)acetaldehyde

Procedure

50 mL of 1N hydrochloric acid is added dropwise to a solution of 10 g (30.88 mmol) of [(E)-2-(2-chloro-4-nitrophenyl)vinyl]dimethylamine in 200 mL of ethanol and the reaction mixture is then refluxed for 1 hour. Then the reaction mixture is evaporated down, diluted with water, and twice extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: petroleum ether/ethyl acetate (3:1)). Yield: 4.5 g (73% of theory); C8H6ClNO3 (M=199.59); Rf value: 0.62 (silica gel, petroleum ether/ethyl acetate (1:1)).

Workup

  1. temperaturethe reaction mixture is then refluxed for 1 hour
  2. customThen the reaction mixture is evaporated down
  3. additiondiluted with water
  4. extractiontwice extracted with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customThe purification

Sources & evidence

ORD record
ord-2731509d264f409c87065ef471fd8da9
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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