Dichloromethane → 2-[4-(Propan-2-yl)phenyl]prop-2-enal

HRID 478149Notes

Reaction equation

HRID 478149 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]=[O:12])=[CH:6][CH:5]=1)[CH3:3].[CH2:13](Cl)Cl.C[N+](C)=C.[I-].[Cl-].[NH4+]>C(N(CC)CC)C>[CH3:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10](=[CH2:13])[CH:11]=[O:12])=[CH:8][CH:9]=1)[CH3:1]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 61359p-IsopropylphenylacetaldehydeHCID 2724133Dimethyl(methylene)ammounium iodide

Product 1

HCID 180009032-[4-(Propan-2-yl)phenyl]prop-2-enal

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4.65 g of aldehyde 43 is introduced into 300 ml of methylene chloride under nitrogen, and 7.9 ml of triethylamine and 6.9 g of Eschenmoser's salt are added at 0° C. After 2.5 hours at 0° C., saturated ammonium chloride solution is added, extracted with methylene chloride, washed with sodium chloride solution, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 3.84 g of title compound 44 accumulates as a colorless oil.

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with sodium chloride solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 3.84 g of title compound 44 accumulates as a colorless oil

Sources & evidence

ORD record
ord-98161666d7d04fcfb2f4fe8ec978131a
Source dataset
uspto-grants-2003_11
Patent number
US06642218B2

Reaction notes

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