Isochromane → 3,4-Dihydroisocoumarin

HRID 2360592Notes

Reaction equation

HRID 2360592 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][O:2]1.[Mn]([O-])(=O)(=O)=[O:12].[K+]>ClCCl.[O-2].[O-2].[Mn+4]>[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][O:2]1

Participants

5

Reactant 2

HCID 96266IsochromaneHCID 516875Potassium Permanganate

Product 1

HCID 784293,4-DihydroisocoumarinYield 80%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of isochroman (5.0 g; 37.3 mmol) in dichloromethane (465 ml) stirred at room temperature was added, over 15 minutes, a homogeneous mixture of potassium permanganate and manganese dioxide (74.60 g) in a 1:3 ratio. The suspension obtained was left for 18 hours at room temperature. The suspension was filtered through a Büchner filter. The solvent was evaporated off under reduced pressure to give 4.42 g of crude product (80%), which was used for the following reaction without further purification.

Workup

  1. additionwas added, over 15 minutes
  2. customThe suspension obtained
  3. filtrationThe suspension was filtered through a Büchner
  4. filtrationfilter
  5. customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-ce341a56600a4fc4af8f9c99f065a678
Source dataset
uspto-grants-2014_04
Patent number
US08686147B2

Reaction notes

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