Acetic Anhydride → 3,6-Dimethoxyphthalic anhydride

HRID 374655Notes

Reaction equation

HRID 374655 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([C:11]([OH:13])=O)[C:4]=1[C:14]([OH:16])=[O:15].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]2[C:14]([O:16][C:11](=[O:13])[C:5]=12)=[O:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 33346443,6-dimethoxyphthalic Acid

Product 1

HCID 27525923,6-Dimethoxyphthalic anhydride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
12 °C

Procedure

3,6-Dimethoxybenzene-1,2-dicarboxylic acid (20 g) was dissolved in pyridine (100 ml) at room temperature. The solution was then cooled in a cold water bath and acetic anhydride (27 g, 25 ml) added dropwise over 10 minutes (temperature rose from 23° to 25° C.) The reaction mixture was then stirred for 90 minutes at 12° C., filtered, washed with ether (100 ml) and pulled dry to give a pale cream solid. Dried at 50° C. in a vacuum oven, m.p. 268°-269° C.

Workup

  1. temperatureThe solution was then cooled in a cold water bath
  2. filtrationfiltered
  3. washwashed with ether (100 ml)
  4. custompulled dry
  5. customto give a pale cream solid
  6. customDried at 50° C. in a vacuum oven, m.p. 268°-269° C.

Sources & evidence

ORD record
ord-8630f2d2e3c543c7a44c1c36bc78bd5a
Source dataset
uspto-grants-1996_01
Patent number
US05480873

Reaction notes

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