1,4-Dioxane → 1-oxo-1,3-dihydroisobenzofuran-5-carbaldehyde

HRID 2180321Notes

Reaction equation

HRID 2180321 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].O1CCOCC1>O1CCCC1.[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 312751,4-DioxaneHCID 98155555-Chlorocarbonylphthalide

Product 1

HCID 98774631-oxo-1,3-dihydroisobenzofuran-5-carbaldehydeYield 48.5%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

In a hydrogenator, 8.2 g (0.042 mole) of 5-chlorocarbonylphthalide, 50 ml of dioxane and 0.77 g of 5% Pd/BaSO4 are charged and the mixture is hydrogenated at 4 bar and 70° C. for 7 hours. After this period of time, the reaction no longer proceeds because of the co-precipitation of the formed product; thus, the hydrogenation is stopped, the mixture is diluted with 120 ml of tetrahydrofuran and stirred at 40° C. for 20 minutes. The solid is filtered off and the solution is concentrated to a little volume. The crystalline product is recovered by filtration and dried to give 3.3 g of 5-formylphthalide with a purity (HPLC)=82% (yield 40%).

Workup

  1. waitAfter this period of time
  2. customthe reaction
  3. filtrationThe solid is filtered off
  4. concentrationthe solution is concentrated to a little volume
  5. filtrationThe crystalline product is recovered by filtration
  6. customdried

Sources & evidence

ORD record
ord-a1a10165d93c439aadf65f81fe4a99d0
Source dataset
uspto-grants-2005_05
Patent number
US06888010B2

Reaction notes

Loading…