Acetic Acid → HCID 67923195, compound

HRID 358564Notes

Reaction equation

HRID 358564 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[S:16]([C:19]1[CH:31]=[CH:30][C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][C:21]=2[CH:20]=1)(=[O:18])=[O:17])([CH3:3])[CH3:2].O.O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:35].[Na+].[Na+].C(O)(=O)C>O>[CH:13]([C:6]1[CH:7]=[C:8]([CH:10]([CH3:11])[CH3:12])[CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]=1[S:16]([C:19]1[C:20](=[O:35])[C:21]2[C:29](=[CH:30][CH:31]=1)[C:28]1[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH:22]=2)(=[O:18])=[O:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 108005Sodium dichromate dihydrateHCID 15054990HCID 15054990, compound

Product 1

HCID 67923195HCID 67923195, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A portion of the 2-(2,4,6-triisopropylphenylsulfonyl)fluorene just described (8.67 g, 20.0 mmol) was placed in a 1 liter flask (equipped with a magnetic stirrer and reflux condenser) along with 17.9 g (60.0 mmol, 3.0 eq) of sodium dichromate dihydrate and 500 ml of glacial acetic acid. The mixture was refluxed for 15 hours, cooled, and poured into 2.0 liters of water. The solids were collected by filtration and washed with additional water (2×1.0 liter). The crude product was dried and purified by chromatography. A total of 3.60 g (8.06 mmol, 40.3%) of pure 2-(2,4,6-triisopropylphenylsulfonyl)fluorenone was obtained in this manner. Its structure was confirmed by IR, NMR, and ultraviolet-visible (UV-VIS) spectroscopy, FDMS, and combustion analysis.

Workup

  1. customwas placed in a 1 liter flask
  2. temperatureThe mixture was refluxed for 15 hours
  3. temperaturecooled
  4. filtrationThe solids were collected by filtration
  5. washwashed with additional water (2×1.0 liter)
  6. dry with materialThe crude product was dried
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-1960066728ee4fd3890b5865bb654960
Source dataset
uspto-grants-1991_03
Patent number
US04997737

Reaction notes

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