Phthalic Anhydride → HCID 15669798, compound

HRID 1721127Notes

Reaction equation

HRID 1721127 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])[CH2:13]C([O-])=O.[K+]>C1(C)C=CC=CC=1>[C:1]1([C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:4](=[CH:13]/[C:12]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])/[O:6]1)=[O:11]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 23662309HCID 23662309, compound

Product 1

HCID 15669798HCID 15669798, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

14.8 g (0.1 mol) of phthalic anhydride and 9.9 g (0.05 mol) of potassium tert-butyl malonate are added to 200 ml of toluene, and the reaction mixture is heated under reflux for 6 hours. After terminating the reaction, 100 ml of water is added, and an organic layer is separated out. The organic layer is washed with 100 ml of 5%-aqueous ammonium bicarbonate solution, and toluene is distilled off under a reduced pressure. The residue thus obtained is purified by column chromatography, to give 6.4 g (0.026 mol) of tert-butyl (Z)-3-phthalidylideneacetate. The yield is 52.0%.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 6 hours
  3. customAfter terminating
  4. customthe reaction, 100 ml of water
  5. additionis added
  6. customan organic layer is separated out
  7. washThe organic layer is washed with 100 ml of 5%-aqueous ammonium bicarbonate solution, and toluene
  8. distillationis distilled off under a reduced pressure
  9. customThe residue thus obtained
  10. customis purified by column chromatography

Sources & evidence

ORD record
ord-c92df21648b34fa4a3977e1cac98b9d0
Source dataset
uspto-grants-1996_04
Patent number
US05508446

Reaction notes

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