Allyl Alcohol → 3-(3-Chlorophenyl)propionaldehyde

HRID 480342Notes

Reaction equation

HRID 480342 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 18 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-527c4a5139ef4781838ecd1b27c2469d
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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