Acetic Anhydride → O-Acetylsyringic Acid

HRID 1830958Notes

Reaction equation

HRID 1830958 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]>O>[C:15]([O:13][C:1](=[O:14])[C:2]1[CH:3]=[C:4]([O:5][CH3:6])[C:7]([OH:8])=[C:9]([O:10][CH3:11])[CH:12]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10742Syringic Acid

Product 1

HCID 86760109O-Acetylsyringic AcidYield 92.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of syringic acid 81 (10.0 g, 50.5 mmol) in acetic anhydride (30.0 g, 27.7 mL, 294.1 mmol) was warmed gently until a clear solution was obtained. Fused sodium acetate (0.5 g, 6.10 mmol) was added to the solution which was allowed to stir for 16 hours at room temperature. The solution was poured into water (100 mL) and stirred thoroughly to ensure hydrolysis of any excess anhydride. Crude O-Acetyl-syringic acid was recrystallized from water to afford the product as an off-white powder (11.2 g, 46.7 mmol). H1 NMR (270 MHz, CDCl3) δ7.36 (s, 2H), 5.94 (br s, 1H), 3.87 (s, 6H), 2.35 (s, 3H). HRMS calcd for 240.0634, found 240.0637

Workup

  1. temperaturewas warmed gently until a clear solution
  2. customwas obtained
  3. stirringstirred thoroughly
  4. customCrude O-Acetyl-syringic acid was recrystallized from water

Sources & evidence

ORD record
ord-296153c183c74566be1864981d95b8c3
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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