Phthalic Anhydride → 3-[(3-Methoxyphenyl)methylidene]-2-benzofuran-1(3H)-one

HRID 840499Notes

Reaction equation

HRID 840499 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1.C1(=O)O[C:16](=[O:17])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12>C([O-])(=O)C.[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[CH:9]=[C:10]1[C:19]2[C:15](=[CH:14][CH:22]=[CH:21][CH:20]=2)[C:16](=[O:17])[O:12]1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 15719(3-Methoxyphenyl)acetic acid

Product 1

HCID 544728733-[(3-Methoxyphenyl)methylidene]-2-benzofuran-1(3H)-oneYield 69.7%

Reagents, catalysts & solvents 1

HCID 517045Sodium AcetateCatalyst

Conditions

Temperature
240 °C

Procedure

A mixture of 15 g (89 mmol) of m-methoxyphenyl acetic acid, 13.2 g (89 mmol) of phthalic anhydride and 246 mg (2.9 mmol) of sodium acetate was heated to 240° C. for 6 hours and water was continuously removed from the reaction. The solid formed in the reaction flask on cooling. This was recrystallized from absolute ethanol to obtain 15.6 g (62 mmol, 69%) of 1 as yellow powder.

Workup

  1. customwater was continuously removed from the reaction
  2. customThe solid formed in the reaction flask
  3. temperatureon cooling
  4. customThis was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-64bd66f01e48450f9d07b723ff12e19a
Source dataset
uspto-grants-2002_04
Patent number
US06368814B1

Reaction notes

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