Dimethylformamide → 4,5-Dimethoxy-2-methylbenzaldehyde

HRID 1605199Notes

Reaction equation

HRID 1605199 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[CH3:12]N(C=O)C.[OH-:17].[Na+]>O>[CH3:12][C:7]1[C:2]([CH:1]=[O:17])=[CH:3][C:4]([O:10][CH3:11])=[C:5]([O:8][CH3:9])[CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 681263,4-Dimethoxytoluene

Product 1

HCID 821414,5-Dimethoxy-2-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Freshly distilled POCL3 (50.6 ml) was added dropwise during 30 min to a stirred mixture of 4 -methylveratrole (65.7 g) and DMF (30 g) freshly distilled after standing two days over CuSO4. Heating overnight on a steam bath under reflux gave a deep brown, viscous solution which when cooled was admixed with 600 ml water. Addition of excess 10% NaOH solution separated out a yellow oil which was extracted with benzene. The combined extracts were washed with water, dried, and evaporated to give a viscous yellow oil. Crystallization from alcohol gave 3.4 g of the aldehyde as a white powder, mp 74°-75°(Lit. 74°). Nmr (δ): 2.58 (s, 3H), 3.90 (s, 3H), 3.95 (s, 3H), 6.68 (s, 1H), 7.30 (s, 1H), 10.20 (s, 1H).

Workup

  1. distillationfreshly distilled
  2. temperatureHeating overnight on a steam bath
  3. temperatureunder reflux
  4. customgave a deep brown, viscous solution which when
  5. temperaturecooled
  6. customseparated out a yellow oil which
  7. extractionwas extracted with benzene
  8. washThe combined extracts were washed with water
  9. customdried
  10. customevaporated
  11. customto give a viscous yellow oil
  12. customCrystallization from alcohol

Sources & evidence

ORD record
ord-8fbe3d498e3e4c779585c2e44d2baa28
Source dataset
uspto-grants-1976_04
Patent number
US03950236

Reaction notes

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