Vanillin → 4-Ethoxy-3-methoxybenzaldehyde

HRID 1639226Notes

Reaction equation

HRID 1639226 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[O:11])[CH:6]=[CH:7][C:8]=1[OH:9].[OH-].[Na+].[CH2:14](I)[CH3:15]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH2:14][CH3:15])[CH:10]=[O:11]

Participants

5

Reactant 3

HCID 1183VanillinHCID 6340IodoethaneHCID 14798Sodium Hydroxide

Product 1

HCID 671164-Ethoxy-3-methoxybenzaldehydeYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 30.4 g (0.2 mole) of vanilline, 12 g (0.3 mole) of sodium hydroxide and 300 ml of water, then 37.4 g (0.24 mole) of ethyl iodide are added. The reaction mixture is heated to boiling for 15 hours, then cooled and extracted with benzene. The extract is evaporated. The crude residue is dissolved in 110 ml of a 25% aqueous sodium hydroxide solution, clarified with activated charcoal and made alkaline to pH 12. The precipitated crystals are filtered, washed with water and dried. Thus 24.8 g of 3-methoxy-4-ethoxy-benzaldehyde are obtained, yield 69%, m.p.: 65°-67° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperaturecooled
  3. extractionextracted with benzene
  4. customThe extract is evaporated
  5. dissolutionThe crude residue is dissolved in 110 ml of a 25% aqueous sodium hydroxide solution
  6. filtrationThe precipitated crystals are filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-6454abf2cb37410ba522734900b5f173
Source dataset
uspto-grants-1989_11
Patent number
US04883798

Reaction notes

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