Iodoethane → 3,4-Diethoxybenzaldehyde

HRID 993137Notes

Reaction equation

HRID 993137 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH3:21]>CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:20][CH3:21])[CH:7]=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8467EthylvanillinHCID 11430Potassium Carbonate

Product 1

HCID 748473,4-DiethoxybenzaldehydeYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Ethoxy-4-hydroxy-benzaldehyde (Aldrich, 100 g, 0.602 mole) was dissolved in N,N-dimethylformamide (1 L). The reaction was placed under N2. Solid potassium carbonate (103 g, 0.662 moles) was added and the reaction was stirred 10 minutes. Iodoethane (175 g, 1.26 moles) was added and the reaction was stirred for 16 hours at room temperature. The reaction was monitored by thin-layer chromatography which indicated complete consumption of the phenol to give a new product. The reaction was filtered to remove the potassium carbonate and solvent removed in vacuo. The residue was dissolved in methylene chloride and filtered. Silica gel (200 g) was added and the dichloromethane removed in vacuo. The crude product absorbed on silica gel was submitted to flash chromatography (hexane, 100%, 2 L, then ethyl acetate:hexane, 1:3, 2 L, then ethyl acetate:hexane, 1:1) to yield 109.36 g of 3,4-diethoxy-benzaldehyde 1HNMR (CDCl3): 9.83 (s, 1H), 7.41 (m, 2H), 6.96 (d, 1H), 4.17 (m, 4H), 1.50 (t, 3H) 1.47 (t, 3H).

Workup

  1. stirringthe reaction was stirred for 16 hours at room temperature
  2. customconsumption of the phenol
  3. customto give a new product
  4. filtrationThe reaction was filtered
  5. customto remove the potassium carbonate and solvent
  6. customremoved in vacuo
  7. dissolutionThe residue was dissolved in methylene chloride
  8. filtrationfiltered
  9. additionSilica gel (200 g) was added
  10. customthe dichloromethane removed in vacuo
  11. customThe crude product absorbed on silica gel

Sources & evidence

ORD record
ord-4065ab8444d0470cafc6e8d3c69e18f8
Source dataset
uspto-grants-2002_10
Patent number
US06472393B1

Reaction notes

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