Sulfuric Acid → Syringaldehyde

HRID 1674453Notes

Reaction equation

HRID 1674453 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>>[CH3:14][O:13][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:10]=1[OH:11])[CH:6]=[O:7]

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 yields 3,5-Dimethoxy-4-hydroxy benzaldehyde (Syringaldehyde). Condensation of syringaldehyde with 2-ethylhexyl acetoacetate 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 1.5 hours for completion. The yield obtained is typically 92%.

Workup

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

Sources & evidence

ORD record
ord-b678cec9a43041ae8c4e60509f0711be
Source dataset
uspto-grants-2011_08
Patent number
US08003082B2

Reaction notes

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