Ethyl Acetate → 4-Iodobenzaldehyde

HRID 1765694Notes

Reaction equation

HRID 1765694 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.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:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 290124-Iodobenzyl alcoholHCID 82029Methyl morpholine oxide

Product 1

HCID 966574-IodobenzaldehydeYield 73%

Reagents, catalysts & solvents 4

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

Procedure

A solution of 4-iodobenzyl alcohol (9 g, 38.29 mmol) in dichloromethane (90 mL) and acetonitrile (10 mL) was treated sequentially with 4 A molecular sieves powder (9 g), tetra-n-propyl ammoniumperruthenate (0.13 g) and N-methyl morpholine-N-oxide (9 g, 76.6 mmol). After stirring at ambient temperature for 2 h, the reaction mixture was diluted with hexane and subjected to flash column chromatography over-silica-gel-(230–400 mesh) using-6–1% ethyl acetate in hexane as the eluent to afford the title compound (2.5 g pure and 4 g˜95% pure, 73%).

Sources & evidence

ORD record
ord-82fc13cbc75a4c6593d8f2580934f391
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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