Acetic Anhydride → 5-Methoxy-1,3-dihydro-2-benzofuran-1,3-dione

HRID 41396Notes

Reaction equation

HRID 41396 reaction equation
C(OC(=O)C)(=O)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:19]([OH:21])=[O:20])[C:13](=[CH:17][CH:18]=1)[C:14]([OH:16])=O>O1CCCC1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:19](=[O:20])[O:21][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 746654-Methoxyphthalic acid

Product 1

HCID 6397485-Methoxy-1,3-dihydro-2-benzofuran-1,3-dioneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (40 ml) was added to a mixture of 4-methoxyphthalic acid (30.8 g, 0.16 mol) in anhydrous tetrahydrofuran (150 ml) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the solvent was removed in vacuo to afford 4-methoxyphthalic anhydride (27.8 g, 99%) as an off white solid. 1H NMR (DMSO-d6) 8.02 (1H, d), 7.59 (1H, d), 7.49 (1H, dd), 3.97 (3H, s). MS: [M+H]+ 179.

Workup

  1. temperatureat reflux for 4 hours
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-e87b3ec236794aee911fea7fee27080c
Source dataset
uspto-grants-2013_09
Patent number
US08530469B2

Reaction notes

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