1(3H)-ISOBENZOFURANONE-3-METHOXYL → Phthalide

HRID 2057510Notes

Reaction equation

HRID 2057510 reaction equation
C[O:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=O)[O:4]1.[H][H]>[Co].CO>[C:3]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:5][O:4]1)=[O:2]

Participants

5

Reactant 2

HCID 3490171(3H)-ISOBENZOFURANONE-3-METHOXYLHCID 178418361HCID 178418361, compound2×

Product 1

HCID 6885PhthalideYield 99%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

The autoclave described in Example 1 is filled with 106.6 g of 3-methoxyphthalide, 400 ml of methanol and 15 g of RCH 45/20 cobalt catalyst (commercial product of Hoechst AG). After the addition of hydrogen to a pressure 100 bars, the autoclave is heated at 120° C., the pressure increasing to about 113 bars. After a temperature of 120° C. is reached, the pressure drops to 100 bars and is brought back up to 120 bars by another injection of hydrogen. After 2 hours of reaction at 120° C., the pressure has dropped again to 100 bars; the mixture is cooled, relieved of pressure, and filtered of catalyst. After withdrawal of the solvent, 86.2 g of phthalide (99% of the theory) is obtained having a melting point of 72°-73° C. (GC analysis 99.2% phthalide).

Workup

  1. temperaturethe pressure increasing to about 113 bars
  2. customAfter a temperature of 120° C.
  3. customAfter 2 hours of reaction at 120° C.
  4. additionthe pressure has dropped again to 100 bars
  5. temperaturethe mixture is cooled
  6. filtrationfiltered of catalyst

Sources & evidence

ORD record
ord-ef4487c6a36543f89c6f3ce858a4dcac
Source dataset
uspto-grants-1980_07
Patent number
US04211711

Reaction notes

Loading…