Pyridine → Acetyl syringic acid

HRID 743050Notes

Reaction equation

HRID 743050 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:13][CH3:14])[C:11]=1[OH:12])[C:6]([OH:8])=[O:7].[C:15](OC(=O)C)(=[O:17])[CH3:16].N1C=CC=CC=1>O>[C:15]([O:12][C:11]1[C:10]([O:13][CH3:14])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10742Syringic Acid

Product 1

HCID 225680Acetyl syringic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3,5-dimethoxy-4-hydroxybenzoic acid (3.00 g) and acetic anhydride (30 ml) was dropwise added pyridine (15 ml) with ice-cooling over a 5 minutes period. After stirring at room temperature for 30 minutes, the reaction mixture was poured into water and stirred at room temperature for 30 minutes followed by extracting thrice with ethyl acetate. The combined extract was washed with 10% hydrochloric acid, dried and concentrated. The residue was recrystallized from a mixture of methylene chloride and hexane to afford the title compound (3.13 g), melting at 192°-194° C.

Workup

  1. temperaturecooling over a 5 minutes period
  2. stirringstirred at room temperature for 30 minutes
  3. extractionby extracting thrice with ethyl acetate
  4. extractionThe combined extract
  5. washwas washed with 10% hydrochloric acid
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was recrystallized from a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-1903ae5281474765b852cb761dea55bd
Source dataset
uspto-grants-1996_09
Patent number
US05556852

Reaction notes

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