Isovanillic Acid → Benzoic acid, 3-(acetyloxy)-4-methoxy-

HRID 1475795Notes

Reaction equation

HRID 1475795 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].[CH3:13][C:14](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:15]>O>[C:14]([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])[CH3:13]

Participants

4

Reactant 2

HCID 12575Isovanillic AcidHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

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 were added to 51.6 g of acetic ahydride and the mixture stirred at 140° C. for 3 h. The mixture was then allowed to cool to 100° C., 50 ml of water added dropwise and the temperature kept at 100° C. Then, 200 ml of water were added and the mixture was stirred at 100° C. for 30 minutes. The mixture was then cooled and stirred at 0° C. for 1 h. The product was then isolated by filtration, washed with 50 ml of water and dried under reduced pressure to yield 18.8 g of the title compound that was used without further purification.

Workup

  1. temperatureto cool to 100° C.
  2. customkept at 100° C
  3. stirringthe mixture was stirred at 100° C. for 30 minutes
  4. temperatureThe mixture was then cooled
  5. stirringstirred at 0° C. for 1 h
  6. customThe product was then isolated by filtration
  7. washwashed with 50 ml of water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-e82bbc25bbf0458d933bf524d67b845d
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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