3-Chlorophthalide → Phthalide

HRID 1763861Notes

Reaction equation

HRID 1763861 reaction equation
Cl[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[O:3]1.C([O-])(=O)C.[Na+].[H][H]>[Pd].C(O)(=O)C>[C:4]1([C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][O:3]1)=[O:5]

Participants

6

Reactant 3

HCID 954693-ChlorophthalideHCID 517045Sodium AcetateHCID 178418361HCID 178418361, compound

Product 1

HCID 6885PhthalideYield 87.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

As described in Example 1, an autoclave is charged with 110 g of 3-chlorophthalide, 5 g of palladium-on-charcoal catalyst (metal content 5%), 54 g of sodium acetate and 400 ml of glacial acetic acid, and treated for 1.5 h with hydrogen at 5 to 10 bars of pressure and 20° to 35° C. After filtration and working up by distillation, 76.5 g of phthalide is obtained, melting point 72°-73° C. (gas-chromatographic analysis 99.35).

Workup

  1. filtrationAfter filtration
  2. distillationworking up by distillation

Sources & evidence

ORD record
ord-ba1572a198a44933b7ac9b2331c2dc4c
Source dataset
uspto-grants-1978_09
Patent number
US04113741

Reaction notes

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