1-Bromopropane → 3-Iodo-5-methoxy-4-propoxybenzaldehyde

HRID 1085631Notes

Reaction equation

HRID 1085631 reaction equation
[CH3:1][CH2:2][CH2:3]Br.[I:5][C:6]1[C:7]([OH:16])=[C:8]([O:14][CH3:15])[CH:9]=[C:10]([CH:13]=1)[CH:11]=[O:12].C(=O)([O-])[O-].[K+].[K+].CCCCCC.C(OCC)(=O)C>CN(C=O)C>[I:5][C:6]1[C:7]([O:16][CH2:1][CH2:2][CH3:3])=[C:8]([O:14][CH3:15])[CH:9]=[C:10]([CH:13]=1)[CH:11]=[O:12]

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-HCID 21226206Ethyl acetate hexane

Product 1

HCID 47701013-Iodo-5-methoxy-4-propoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

n-Propyl bromide (29.2 mL, 0.32 mol) was added to a solution of 5-iodovanillin (50.0 g, 0.18 mol) in DMF (200 mL) containing potassium carbonate (48 g, 0.35 mol) at 80° C. The mixture was stirred at 80° C. for 1-1.5 hours or until TLC (SiO2, 4:1 [v/v] hexane-ethyl acetate) showed the reaction to be complete. The mixture was cooled and the solvent was decanted into ice-water (1 L). The product was extracted with ether and the ethereal layer was washed with water, dried over sodium sulfate, and evaporated in vacuo to an oil, which was used without further purification. Anal. calc. for C11H15IO3 : C, 41.27; H, 4.09. Found: C, 41.59; H, 4.15.

Workup

  1. customthe reaction
  2. temperatureThe mixture was cooled
  3. customthe solvent was decanted into ice-water (1 L)
  4. extractionThe product was extracted with ether
  5. washthe ethereal layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo to an oil, which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-369ab439926048c882d6d44685a7e408
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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