Acetic Acid → 2H,5H-Indeno[5,6-d][1,3]dioxole

HRID 1195269Notes

Reaction equation

HRID 1195269 reaction equation
O[CH:2]1[C:10]2[C:5](=[CH:6][C:7]3[O:13][CH2:12][O:11][C:8]=3[CH:9]=2)[CH2:4][CH2:3]1.C(O)(=O)C.O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH2:12]1[O:11][C:8]2[CH:9]=[C:10]3[C:5]([CH:4]=[CH:3][CH2:2]3)=[CH:6][C:7]=2[O:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 14514900HCID 14514900, compound

Product 1

HCID 190016832H,5H-Indeno[5,6-d][1,3]dioxoleYield 92.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 10.8 g of 1-hydroxy-5,6-methylenedioxyindane and 15 ml of acetic acid in 100 ml of toluene was heated under reflux for 4 h. Water and a small amount of potassium carbonate were added to the reaction mixture. After extraction with ethyl acetate, the organic layer was washed with water and an aqueous common salt solution and dried over magnesium sulfate. The solvent was distilled off and the residue was treated according to silica gel column chromatography (chloroform/hexane=1:3) to obtain 9.0 g of the intended compound in the form of colorless crystals.

Workup

  1. temperatureunder reflux for 4 h
  2. extractionAfter extraction with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialan aqueous common salt solution and dried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. additionthe residue was treated

Sources & evidence

ORD record
ord-ed6bbbf5fddd443998b5d023fc0e6336
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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