Ethyl Bromide → 3-Ethoxy-4-methoxybenzaldehyde

HRID 1605198Notes

Reaction equation

HRID 1605198 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[OH-].[K+].[CH2:14](Br)[CH3:15]>C(O)C.O>[CH2:14]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6])[CH3:15]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 12127IsovanillinHCID 14797Potassium Hydroxide

Product 1

HCID 2447283-Ethoxy-4-methoxybenzaldehydeYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 100 g of 3-hydroxy-4-methoxybenzaldehyde in 200 ml ethanol was added to solution of 44 g KOH in 44 ml H2O. The mixture dissolved upon heating to reflux and 56 ml ethyl bromide was then added slowly. A yellow solid began to precipitate after 15 min and heating of the mixture at reflux was continued overnight. Excess ethyl bromide and solvent were removed in vacuo and the residue was distributed between water and CHCl3. The CHCl3 layer was dried and evaporated to give a pale yellow oil which crystallized from ethanol to give 112 g (93%) of 3-ethoxy-4-methoxybenzaldehyde, mp 49.5°-50.5°(Lit.12 mp 50° -51°).

Workup

  1. dissolutionThe mixture dissolved
  2. temperatureupon heating
  3. temperatureto reflux
  4. customto precipitate after 15 min
  5. temperatureheating of the mixture
  6. temperatureat reflux
  7. customExcess ethyl bromide and solvent were removed in vacuo
  8. dry with materialThe CHCl3 layer was dried
  9. customevaporated
  10. customto give a pale yellow oil which
  11. customcrystallized from ethanol

Sources & evidence

ORD record
ord-1451e10bb33e417fb071cc7f84d4caea
Source dataset
uspto-grants-1976_04
Patent number
US03950236

Reaction notes

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