2-(1-Naphthylmethylene)glutaric acid → 2-(1-Naphthylmethylene)glutaric anhydride

HRID 1768598Notes

Reaction equation

HRID 1768598 reaction equation
[C:1]1([CH:11]=[C:12]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[C:13]([OH:15])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>C(OC(=O)C)(=O)C>[C:1]1([CH:11]=[C:12]2[CH2:16][CH2:17][C:18](=[O:19])[O:20][C:13]2=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 539440592-(1-Naphthylmethylene)glutaric acid

Product 1

HCID 544510142-(1-Naphthylmethylene)glutaric anhydrideYield 86.8%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 10 g (37 mmole) of the 2-(1-naphthylmethylene)glutaric acid prepared as described above and 100 ml of acetic anhydride was stirred at 60° C. for 1 hour. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was triturated with a 1: 1 by volume mixture of benzene and hexane to precipitate crystals, which were collected by filtration to give 8.1 g of 2-(1-naphthylmethylene)glutaric anhydride.

Workup

  1. customprepared
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. customthe resulting residue was triturated with a 1: 1 by volume mixture of benzene and hexane
  4. customto precipitate crystals, which
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-9683674c0df142d5a04c62da82cfbd46
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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