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

HRID 2057478Notes

Reaction equation

HRID 2057478 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=O.C(OC(=O)C)(=O)C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:12](=[O:13])[O:14][C:7](=[O:9])[C:6]2=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 746654-Methoxyphthalic acid

Product 1

HCID 6397485-Methoxy-1,3-dihydro-2-benzofuran-1,3-dione

Procedure

4-Methoxyphthalic acid (959 gm., 5.06 m) and acetic anhydride (2 l.) were mixed together and warmed to reflux. After 2 hours at reflux the solution was filtered while hot. The filtrate was cooled to room temperature and then it was cooled at -70° C. overnight. The solid precipitate was recovered by suction filtration, washed with petroleum ether (40°-60°) and air dried. wt.=649 gm., m.p. 89°-94° C.

Workup

  1. temperaturewarmed to reflux
  2. temperatureAfter 2 hours at reflux the solution
  3. filtrationwas filtered while hot
  4. temperatureit was cooled at -70° C. overnight
  5. filtrationThe solid precipitate was recovered by suction filtration
  6. washwashed with petroleum ether (40°-60°) and air
  7. customdried

Sources & evidence

ORD record
ord-b97e3eb889044cedab1121d55ccb18ad
Source dataset
uspto-grants-1980_07
Patent number
US04210749

Reaction notes

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