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

HRID 2180320Notes

Reaction equation

HRID 2180320 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].N1C2C(=CC=CC=2)C=CC=1.[S]>[Pd].O1CCCC1>[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 178527711HCID 178527711, compound

Product 1

HCID 98774631-oxo-1,3-dihydroisobenzofuran-5-carbaldehydeYield 68.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7 g (0.036 mole) of 5-chlorocarbonylphthalide, 50 ml of tetrahydrofuran, 0.1 ml of the quinoline/sulfur mixture and 1 g of 10% Pd/C is hydrogenated at 3.5 bar and 35÷40° C. for 3 hours. After 3 hours a stoppage of the hydrogen absorption is observed. Thus, the mixture is cooled, diluted with dichloromethane, filtered, and by a HPLC control the presence of equivalent amounts of alcohol and aldehyde is observed. The mixture is concentrated under vacuum and the residue is taken up with ethyl acetate. The crystalline product is filtered and dried to obtain 4 g of 5-formylphthalide with a purity (HPLC)=44% (yield 30%).

Workup

  1. customAfter 3 hours a stoppage of the hydrogen absorption
  2. temperatureThus, the mixture is cooled
  3. additiondiluted with dichloromethane
  4. filtrationfiltered
  5. concentrationThe mixture is concentrated under vacuum
  6. filtrationThe crystalline product is filtered
  7. customdried

Sources & evidence

ORD record
ord-71038019ff3144959bb5e0a3d4f805f4
Source dataset
uspto-grants-2005_05
Patent number
US06888010B2

Reaction notes

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