Water → 4-Ethoxy-3-methoxybenzaldehyde

HRID 483676

Reaction equation

HRID 483676 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:22][CH3:23])(=O)=O.O>C(#N)C>[CH2:22]([O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 6163Diethyl SulfateHCID 11430Potassium Carbonate

Product 1

HCID 671164-Ethoxy-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Vanillin (10 g., 66 mmol) in acetonitrile (100 ml) was treated with finely-powdered, anhydrous potassium carbonate (12 g., 87 mmol) with vigorous stirring to yield a mobile suspension. Diethyl sulfate (11 ml, 84 mmol) was added at room temperature. The suspension was brought to reflux, becoming quite thick after 10 minutes, but thinning again after 20 minutes. Refluxing was continued for 48 hours, at which point water (5 ml) was added. After an additional 2 hours of reflux, the mixture was cooled and treated with 500 ml ice water. Stirring at 0° for several hours produced a granular precipitate which was filtered off and washed with water. Air drying afforded 11.5 g. of the product (97%) as an off-white solid melting at 61°-62.5° C. NMR and IR data are listed in Tables 3 and 7. ##STR25##

Workup

  1. customto yield a mobile suspension
  2. temperatureto reflux
  3. waitthinning again after 20 minutes
  4. temperatureRefluxing
  5. additionwas added
  6. temperatureAfter an additional 2 hours of reflux
  7. temperaturethe mixture was cooled
  8. stirringStirring at 0° for several hours
  9. customproduced a granular precipitate which
  10. filtrationwas filtered off
  11. washwashed with water
  12. customAir drying
  13. customafforded 11.5 g

Sources & evidence

ORD record
ord-86125cbd7f184984957a5c1e876debb9
Source dataset
uspto-grants-1993_07
Patent number
US05225584

Linked notes

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