Syringaldehyde → 3,4,5-Trimethoxybenzaldehyde

HRID 1262736Notes

Reaction equation

HRID 1262736 reaction equation
[CH:1](=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].S(OC)(OC)=O>CN(C)C=O>[CH3:11][O:10][C:9]1[CH:12]=[C:2]([CH:3]=[C:4]([O:5][CH3:6])[C:7]=1[O:8][CH3:14])[CH:1]=[O:13]

Participants

5

Reactant 3

HCID 8655SyringaldehydeHCID 11430Potassium CarbonateHCID 69223Dimethyl sulfite

Product 1

HCID 68583,4,5-TrimethoxybenzaldehydeYield 56.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a three-neck flask (capicity 100 ml) equipped with a mechanical stirrer and reflux condenser, 20 ml of dimethylformamide, 10.0 g (0.054 mol) of syringaldehyde and 5.00 g (0.036 mol) of anhydrous potassium carbonate were placed and the mixture was heated under a nitrogen atmosphere to 100° C. To this mixture was added 8.00 ml (0.094 mol) of dimethyl sulfite. The mixture was maintained at about 100° C. for eight hours and then cooled to 25° C. and quenched with 500 ml water. The mixture was extracted with 100 ml of methylene chloride. The extracts were washed with water and concentrated in vacuo to give 4.0 g of 3, 4, 5-trimethoxybenzaldehyde.

Workup

  1. customIn a three-neck flask (capicity 100 ml) equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe mixture was maintained at about 100° C. for eight hours
  4. temperaturecooled to 25° C.
  5. customquenched with 500 ml water
  6. extractionThe mixture was extracted with 100 ml of methylene chloride
  7. washThe extracts were washed with water
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-522e209d018348128b6cb07be23166ee
Source dataset
uspto-grants-1984_06
Patent number
US04453018

Reaction notes

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