Ethyl Acetate → 3-Iodobenzaldehyde

HRID 1765698Notes

Reaction equation

HRID 1765698 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].C[N+]1([O-])CCOCC1.C(OCC)(=O)C>ClCCl.C(#N)C.CCCCCC.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 423003-Iodobenzyl alcoholHCID 82029Methyl morpholine oxide

Product 1

HCID 2526103-IodobenzaldehydeYield 80%

Reagents, catalysts & solvents 4

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent2×

Procedure

A solution of 3-iodobenzyl alcohol (Aldrich, 4.72 g, 20 mmol) in dichloromethane (50 mL) and acetonitrile (5 mL) was treated sequentially with 4 A molecular sieves powder (5 g), tetra-n-propyl ammoniumperruthenate (0.1 g) and N-methyl morpholine-N-oxide (2.34 g, 40 mmol). After stirring at ambient temperature for 3 h, the reaction mixture was diluted with hexane and subjected to flash column chromatography over silica gel (230–400 mesh) using 6–10% ethyl acetate in hexane as the eluent to afford the title compound (3.7 g, 80%). It was used as such for the next step.

Sources & evidence

ORD record
ord-12c7370ce95e4fc0b36a1eccdde2f61d
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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