Dichloromethane → 4-Methylphenyl-2-propenal

HRID 1359545Notes

Reaction equation

HRID 1359545 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]=[O:10])=[CH:4][CH:3]=1.[CH2:11](Cl)Cl.C[N+](C)=C.[I-].[Cl-].[NH4+]>C(N(CC)CC)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:11])[CH:9]=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 61006Lilac acetaldehydeHCID 2724133Dimethyl(methylene)ammounium iodide

Product 1

HCID 180009044-Methylphenyl-2-propenal

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2.57 g of aldehyde 37 is introduced into 300 ml of methylene chloride under nitrogen, and 6.5 ml of triethylamine and 7.1 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 1.94 g of title compound 38 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 1.94 g of title compound 38 accumulates as a colorless oil

Sources & evidence

ORD record
ord-c1a219dc11c04ea39e0ffd325dee711f
Source dataset
uspto-grants-2003_07
Patent number
US06600058B1

Reaction notes

Loading…