Peracetic Acid → Indanofan

HRID 1461634Notes

Reaction equation

HRID 1461634 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH2:10][C:11]2([CH2:22][CH3:23])[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])=[CH2:9])[CH:5]=[CH:6][CH:7]=1.O.O.O.C([O-])(=[O:29])C.[Na+].C(OO)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([O:29][CH2:9]2)[CH2:10][C:11]2([CH2:22][CH3:23])[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6585Peracetic AcidHCID 24477Sodium ThiosulfateHCID 111311612-[2-(3-Chlorophenyl)prop-2-enyl]-2-ethylindene-1,3-dioneHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 11046097IndanofanYield 149.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To the mixture of 1.62 g of 2-[2-(3-chlorophenyl) propen 3-yl]-2-ethylindan-1,3-dione, 0.34 g of sodium acetate trihydrate and 10 ml of chloroform was added-2.85 g of 40% peracetic acid. After refluxing for 3 hours, excess peroxide was decomposed with 10% sodium thiosulfate aqueous solution, and the organic layer was washed with water, neutralized with a saturated sodium bicarbonate aqueous solution, washed with water and with a saturated saline solution, and dried over anhydrous magnesium sulfate. After the solvent was evaporated, the residue was separated and purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=4/1) to obtain 1.27 g of the compound No. 53 shown in Table 2.

Workup

  1. temperatureAfter refluxing for 3 hours
  2. washthe organic layer was washed with water
  3. washwashed with water and with a saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was evaporated
  6. customthe residue was separated
  7. custompurified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-3e5eb27454a647848e0b2cf9039fb8bf
Source dataset
uspto-grants-1991_12
Patent number
US05076830

Reaction notes

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