Sulfuric Acid → HCID 21842016, compound

HRID 1737286Notes

Reaction equation

HRID 1737286 reaction equation
[CH:1]([O:4][P:5]([O:22][CH:23]([CH3:25])[CH3:24])([CH:7]([P:12]([O:18][CH:19]([CH3:21])[CH3:20])([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:9][CH2:10][OH:11])=[O:6])([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:27].C(O)(C)C.C(=O)([O-])O.[Na+]>CC(C)=O.O.[O-2].[O-2].[O-2].[Cr+6]>[CH:15]([O:14][P:12]([O:18][CH:19]([CH3:21])[CH3:20])([CH:7]([P:5]([O:22][CH:23]([CH3:25])[CH3:24])([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:8][CH2:9][C:10]([OH:27])=[O:11])=[O:13])([CH3:16])[CH3:17]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 21842003HCID 21842003, compound

Product 1

HCID 21842016HCID 21842016, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

Under a nitrogen atmosphere, 4,4-bis(diisopropoxyphosphinoyl)-1-butanol (10.12 g) was dissolved in acetone (30 ml), and the resulting solution was cooled to 0-5° C. A solution of chromium trioxide (2.7 g) and concentrated sulfuric acid (2.3 ml) in water (8 ml) was added dropwise thereto, and the resulting mixture was stirred at 0-5° C. for 2 hours. The mixture was stirred at room temperature for another 10 hours, and then isopropanol (15 ml) was added dropwise thereto and stirred for 30 minutes. The resulting mixture was neutralized with a saturated aqueous sodium hydrogencarbonate solution and the insoluble materials were removed by filtration through Celite. The filtrate was acidified with hydrochloric acid and extracted three times with chloroform, and the organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 4,4-bis(diisopropoxyphosphinoyl)butyric acid (6.75 g, yield 64%).

Workup

  1. stirringThe mixture was stirred at room temperature for another 10 hours
  2. stirringstirred for 30 minutes
  3. customthe insoluble materials were removed by filtration through Celite
  4. extractionextracted three times with chloroform
  5. washthe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1e18cf56bb647dca3df125f96f85360
Source dataset
uspto-grants-1999_10
Patent number
US05962438

Reaction notes

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