Syringaldehyde → 3,4,5-Trimethoxybenzaldehyde

HRID 1262707Notes

Reaction equation

HRID 1262707 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>>[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

4

Reactant 3

HCID 8655SyringaldehydeHCID 11430Potassium CarbonateHCID 69223Dimethyl sulfite

Product 1

HCID 68583,4,5-TrimethoxybenzaldehydeYield 59.5%

Conditions

Temperature
100 °C

Procedure

In an apparatus as in Example 1, 10.0 g (0.054 mol) of syringaldehyde and 5.00 g (0.036 mol) of potassium carbonate were heated to 100° C. and 8 ml (0.094 mol) of dimethyl sulfite was added over a 5 minute period. The pasty mixture was heated to 100° C. for 3 hours then cooled to 25° C. and quenched with 50 ml water. The mixture was extracted with 100 ml of methylene chloride. The extracts were washed with water and concentrated in vacuo to get 4.2 g (54% based on recovered syringaldehyde) of 3,4,5-trimethoxybenzaldehyde.

Workup

  1. temperaturethen cooled to 25° C.
  2. customquenched with 50 ml water
  3. extractionThe mixture was extracted with 100 ml of methylene chloride
  4. washThe extracts were washed with water
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7df6821df40414f9c4e551048f848b3
Source dataset
uspto-grants-1984_06
Patent number
US04453004

Reaction notes

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