Sulfuric Acid → Syringaldehyde

HRID 394419Notes

Reaction equation

HRID 394419 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11]C)[CH:6]=[O:7].S(=O)(=O)(O)O>>[CH:6](=[O:7])[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:10]([OH:11])=[C:9]([O:13][CH3:14])[CH:8]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 68583,4,5-Trimethoxybenzaldehyde

Product 1

HCID 8655Syringaldehyde

Procedure

Monodemethylation of 3,4,5-trimethoxybenzaldehyde using sulphuric acid at 40° C. for 8 hours as described above in Example 1 yields syringaldehyde. Condensation of 3,5-Dimethoxy-4-hydroxy benzaldehyde (Syringaldehyde) with diethyl malonate in the presence of piperidine—acetic acid and benzene as the reaction medium at reflux temperature under continuous azeotropic water removal yields the title product. The reaction takes about 7.5 hours for completion.

Workup

  1. customat 40° C.
  2. customfor 8 hours

Sources & evidence

ORD record
ord-2e39e66ff7c24d00b7beffd640da10ae
Source dataset
uspto-grants-2003_08
Patent number
US06602515B2

Reaction notes

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