Phthalic Anhydride → HCID 54118976, compound

HRID 1637650Notes

Reaction equation

HRID 1637650 reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[Br:12][C:13]1[CH:14]=[C:15]([CH2:19]C(O)=O)[CH:16]=[CH:17][CH:18]=1.C([O-])(=O)C.[Na+]>C(O)C>[Br:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[CH:19]=[C:1]1[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[O:6]1

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 74653(3-Bromophenyl)acetic acidHCID 517045Sodium Acetate

Product 1

HCID 54118976HCID 54118976, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of phthalic acid anhydride (43 g, 0.291 mol), 3-bromophenyl acetic acid (62.5 g, 0.291 mol) and sodium acetate (2 g, 0.015 mol) was heated at 220° C. for 2 h under an atmosphere of nitrogen. The reaction mixture was cooled to about 80° C. and ethanol (75 ml) was added. The precipitate was filtered off, washed with a mixture of heptane and ethanol (9:1) and dried in vacuo at 50° C. which afforded 71 g (81%) of 3-(3-bromobenzylidene)-3H-isobenzofuran-1-one as a solid.

Workup

  1. temperatureThe reaction mixture was cooled to about 80° C.
  2. filtrationThe precipitate was filtered off
  3. washwashed with a mixture of heptane and ethanol (9:1)
  4. customdried in vacuo at 50° C. which

Sources & evidence

ORD record
ord-dff6c9af89644b3cbc3e0b28a0a58f03
Source dataset
uspto-grants-2000_03
Patent number
US06043247

Reaction notes

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