Veratraldehyde → 3,4-Dimethoxytoluene

HRID 1605195Notes

Reaction equation

HRID 1605195 reaction equation
[CH:1](=O)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.[OH-].[K+].NN>C(O)CO>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 8419VeratraldehydeHCID 9321HydrazineHCID 14797Potassium Hydroxide2×

Product 1

HCID 681263,4-DimethoxytolueneYield 78.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of veratraldehyde (91.5g), KOH (100 g), 95% hydrazine (75 ml) and ethylene glycol (700 ml) was heated at reflux until the KOH disappeared (30 min). The hydrazone then separated as a yellow solid and mild foaming occurred. The heating was continued at reflux causing evolution of N2 and vigorous frothing. After 3 hr., the solution was cooled, poured into 1.5 l of cold water and the resulting oil was extracted into ether. The combined extracts were washed with water, dried and evaporated to yield a yellow oil which was distilled to give 65.7 g of the product, 3,4-dimethoxy toluene as a colorless oil (bp 68°-72°at 0.05 mm).

Workup

  1. temperaturewas heated
  2. custom(30 min)
  3. customThe hydrazone then separated as a yellow solid and mild foaming
  4. temperatureat reflux
  5. temperature, the solution was cooled
  6. additionpoured into 1.5 l of cold water
  7. extractionthe resulting oil was extracted into ether
  8. washThe combined extracts were washed with water
  9. customdried
  10. customevaporated
  11. customto yield a yellow oil which
  12. distillationwas distilled

Sources & evidence

ORD record
ord-e415a913d2a443129503cc1657aca462
Source dataset
uspto-grants-1976_04
Patent number
US03950236

Reaction notes

Loading…