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

HRID 1375200Notes

Reaction equation

HRID 1375200 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]>[Pd].[O-]S([O-])(=O)=O.[Ba+2].CN(C)C(=O)C>[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 65.1%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

In a hydrogenator, 23 l of N,N-dimethylacetamide, 1.65 Kg (8.39 moles) of 5-chlorocarbonylphthalide (prepared for example as described in J. Chem. Soc., 1931, 867–871) and 200 g of 5% Pd/BaSO4 are charged Hydrogen is then charged at 3 bar thereinto and the mixture is heated at 60±3° C. for a total of 48 hours. The mixture is cooled and, after removal of the catalyst by filtration, the filtrate is concentrated under vacuum at 75° C. up to a solid residue. The product is dispersed with 8 l of deionized water and, at 5÷10° C. under stirring, the pH of the mixture is adjusted to 7.0÷7.5 by addition of 2.3 l of 10% ammonium hydroxide solution After a 30-minute stirring, the product is filtered, washed with deionized water and dried under vacuum at 50° C. to give 885 g (65%) of desired product having m.p.=163÷165° C. (in J. Chem Soc. 1925, page 2290 a m.p.=159÷160° C. is given).

Workup

  1. additionis then charged at 3 bar
  2. temperatureThe mixture is cooled
  3. customafter removal of the catalyst
  4. filtrationby filtration
  5. concentrationthe filtrate is concentrated under vacuum at 75° C. up to a solid residue
  6. additionThe product is dispersed with 8 l of deionized water and, at 5÷10° C.
  7. additionthe pH of the mixture is adjusted to 7.0÷7.5 by addition of 2.3 l of 10% ammonium hydroxide solution After a 30-minute
  8. stirringstirring
  9. filtrationthe product is filtered
  10. washwashed with deionized water
  11. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-cf6284f501b245d58241db63ca7d59a3
Source dataset
uspto-grants-2007_01
Patent number
US07166729B2

Reaction notes

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