Allyl Alcohol → 3-(3-Chlorophenyl)propionaldehyde

HRID 2117591Notes

Reaction equation

HRID 2117591 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.[CH2:9]([OH:12])[CH:10]=[CH2:11].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:11][CH2:10][CH:9]=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 7858Allyl AlcoholHCID 122691-Chloro-3-iodobenzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 104195793-(3-Chlorophenyl)propionaldehydeYield 74%

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-chloro-3-iodobenzene (9.63 g, 40.38 mmol), allyl alcohol (5.86 g, 100.96 mmol), sodium bicarbonate (8.48 g, 100.96 mmol), tetrabutylammonium chloride (11.22 g, 40.38 mmol), and Pd(OAc)2 (317 mg, 1.413 mmol) in 25 mL DMF was stirred at 50° C. for 16 h. The mixture was cooled to room temperature, diluted with water, and the aqueous solution was washed with EtOAc. The organic solution was washed with water followed by brine, dried over MgSO4, filtered and concentrated in vacuo. The product was purified via flash chromatography on silica gel (9:1 hexanes:EtOAc) to afford the title compound as an oil (5.04 g).

Workup

  1. washthe aqueous solution was washed with EtOAc
  2. washThe organic solution was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified via flash chromatography on silica gel (9:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-ce957e3b21704efeb4f9956df56c41e0
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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