Acetic Anhydride → Acetyl syringic acid

HRID 987013Notes

Reaction equation

HRID 987013 reaction equation
[C:1]([OH:14])(=[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:15](OC(=O)C)(=[O:17])[CH3:16]>N1C=CC=CC=1>[C:15]([O:8][C:7]1[C:9]([O:10][CH3:11])=[CH:12][C:2]([C:1]([OH:14])=[O:13])=[CH:3][C:4]=1[O:5][CH3:6])(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10742Syringic Acid

Product 1

HCID 225680Acetyl syringic acidYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 100 ml flask, under a nitrogen atmosphere, 1.50 g (7.57 mmoles) of syringic acid is dissolved in 15 ml of dry pyridine. 0.86 ml (9.08 mmoles) of acetic anhydride is added dropwise and the mixture is agitated at ambient temperature for 18 hours. The pyridine is evaporated off under reduced pressure, the residue is taken up in 25 ml of dichloromethane and washed with 10 ml of a molar solution of HCl then with 2×10 ml of water. The organic phase is dried over sodium sulphate, filtered and evaporated under vacuum. 1.72 g (95%) of a beige powder is obtained. Melting point: 181-183° C.

Workup

  1. customThe pyridine is evaporated off under reduced pressure
  2. washwashed with 10 ml of a molar solution of HCl
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-af921b9f743a4c1c94cb248191902814
Source dataset
uspto-grants-2003_10
Patent number
US06630461B2

Reaction notes

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