Sulfuric Acid → Syringaldehyde

HRID 394422Notes

Reaction equation

HRID 394422 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-trimethoxy benzaldehyde 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 ethyl acetoacetate in the presence of piperidine—acetic acid and benzene as the reaction medium at reflux temperature yields the title product. The reaction takes about 3.5 hours for completion.

Workup

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

Sources & evidence

ORD record
ord-18d9827df8564828ac0a726963d5eabc
Source dataset
uspto-grants-2003_08
Patent number
US06602515B2

Reaction notes

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