Acetic Anhydride → Benzoic acid, 3-(acetyloxy)-4-methoxy-

HRID 1918328Notes

Reaction equation

HRID 1918328 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].[C:13](OC(=O)C)(=[O:15])[CH3:14]>O>[C:13]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12575Isovanillic Acid

Product 1

HCID 151620Benzoic acid, 3-(acetyloxy)-4-methoxy-Yield 88.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
140 °C

Procedure

17.0 g of 3-hydroxy-4-methoxy-benzoic acid and 51.6 g of acetic anhydride were combined and stirred at 140° C. for 3 h. Then 50 ml of water were added at 100° C., the mixture was heated under reflux for 30 min, another 200 ml of water were added and the mixture heated under reflux for 30 min. The mixture was cooled to 0° C., and the product was filtered off, washed with water and dried in vacuo to yield 18.8 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 30 min
  5. temperatureThe mixture was cooled to 0° C.
  6. filtrationthe product was filtered off
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-c5da894ed4c04b3f9d32f97102c00bdb
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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