5-Chlorocarbonylphthalide → 1-oxo-1,3-dihydroisobenzofuran-5-carbaldehyde

HRID 2180318Notes

Reaction equation

HRID 2180318 reaction equation
Cl[C:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH2:7]2)=[O:3].[H][H]>CN(C)C(=O)C.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH2:7]2)=[O:3]

Participants

5

Reactant 2

HCID 98155555-ChlorocarbonylphthalideHCID 178418361HCID 178418361, compound

Product 1

HCID 98774631-oxo-1,3-dihydroisobenzofuran-5-carbaldehydeYield 63.1%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 8.58 g (0.043 mole) of 5-chlorocarbonylphthalide in 120 ml of N,N-dimethylacetamide in a hydrogenator 1 g of 5% Pd/BaSO4 is added and hydrogen at 2.5 bar is charged thereinto. The mixture is heated to 60° C., kept at this temperature for 40 hours at 2.5÷3 bar, then cooled, filtered to remove the catalyst and concentrated under vacuum at 75° C. The residue is taken up with 50 ml of deionized water, then the suspension is neutralized with 10% ammonium hydroxide solution to a pH=7.5 and the product is filtered to give 4.4 g (63%) of 5-formylphthalide with m.p.=162÷163° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customto remove the catalyst
  4. concentrationconcentrated under vacuum at 75° C
  5. filtrationthe product is filtered

Sources & evidence

ORD record
ord-61324664cfa74b5ea61f2311ee95aea7
Source dataset
uspto-grants-2005_05
Patent number
US06888010B2

Reaction notes

Loading…