Diethyl Ether → 3-Iodo-4,5-dimethoxybenzaldehyde

HRID 2294226Notes

Reaction equation

HRID 2294226 reaction equation
I[C:2]([C:4]1[CH:12]=C[C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)=[O:3].[C:13](=O)([O-])[O-].[K+].[K+].[I:19][CH3:20].C(OCC)C>CN(C)C=O>[I:19][C:20]1[CH:12]=[C:4]([CH:5]=[C:6]([O:7][CH3:8])[C:9]=1[O:10][CH3:13])[CH:2]=[O:3]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 53732425Iodovanillin

Product 1

HCID 27781133-Iodo-4,5-dimethoxybenzaldehydeYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred, cooled (0° C.) solution of iodovanillin (10.0 g, 35.96 mmol.) in dimethylformamide (50 mL) was added anhydrous potassium carbonate (20.0 g, 143.86 mmol.) followed by iodomethane (3.11 mL, 50.0 mmol.). The mixture was allowed to warm to ambient temperature and stir for 14 H. The mixture was poured into diethyl ether (500 mL) and washed with water (3×150 mL). The organic phase was dried over MgSO4 and concentrated under reduced pressure to afford 3-iodo-4,5-dimethoxybenzaldehyde (9.5 g) as a yellow oil which solidified upon standing and was used without further purification.

Workup

  1. washwashed with water (3×150 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5141b26bdfc14e139e298ac1d1b355c3
Source dataset
uspto-grants-1997_11
Patent number
US05688807

Reaction notes

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