Dimethylformamide → Veratraldehyde

HRID 1262738Notes

Reaction equation

HRID 1262738 reaction equation
C(=O)[C:2]1[CH:9]=[CH:8][C:6](O)=[C:4]([OH:5])[CH:3]=1.[C:11](=[O:14])([O-])[O-].[K+].[K+].S([O:21][CH3:22])(OC)=O.[CH3:23]N(C)C=O>>[CH:11](=[O:14])[C:2]1[CH:9]=[CH:8][C:6]([O:21][CH3:22])=[C:4]([O:5][CH3:23])[CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 69223Dimethyl sulfite

Product 1

HCID 8419Veratraldehyde

Procedure

To a three-necked 100 ml flask equipped for reflux and fitted with a mechanical stirrer was added 10 ml of dimethylformamide, 1.0 g (0.0072 mol) of protocatechualdehyde 1.0 g (0.007 mol) of potassium carbonate, and 4.0 ml (0.047 mol) of dimethyl sulfite. The mixture was heated for four hours to 100° C. then quenched hot with 200 ml of water. The organic material was extracted into methylene chloride and the extracts were washed with 15 ml of 12% caustic solution, twice with 25 ml of water and then concentrated in vacuo to obtain 0.4 g of crude veratraldehyde.

Workup

  1. customTo a three-necked 100 ml flask equipped
  2. temperaturefor reflux
  3. customfitted with a mechanical stirrer
  4. temperatureThe mixture was heated for four hours to 100° C.
  5. customthen quenched hot with 200 ml of water
  6. extractionThe organic material was extracted into methylene chloride
  7. washthe extracts were washed with 15 ml of 12% caustic solution, twice with 25 ml of water
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-875e5fbc71464e64af29bbd9a2239ad5
Source dataset
uspto-grants-1984_06
Patent number
US04453018

Reaction notes

Loading…