Methanesulfonic Acid → Phosphorus Pentoxide-Methanesulfonic Acid

HRID 1665434Notes

Reaction equation

HRID 1665434 reaction equation
[O:1]=[P:2]12[O:13][P:11]3([O:14][P:4]([O:6][P:7]([O:10]3)([O:9]1)=[O:8])(=[O:5])[O:3]2)=[O:12].[CH3:15][S:16]([OH:19])(=[O:18])=[O:17]>C(OCC)(=O)C>[CH3:15][S:16]([OH:19])(=[O:18])=[O:17].[O:5]=[P:4]12[O:3][P:2]3([O:9][P:7]([O:10][P:11]([O:13]3)([O:14]1)=[O:12])(=[O:8])[O:6]2)=[O:1]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Eaton's reagent was prepared by stirring P2O5 (1.0 g) in methane sulfonic acid (10 mL) at rt for 12 h. ISA (2 g) was added to the Eatons reagent and heated at 120° C. for 2 h. The reaction mixture was cooled to rt, quenched with ice and extracted with ethyl acetate. Combined organic layer was washed with 10% NaHCO3 solution (2×100 mL), water (1×100 mL), brine (1×100 mL), dried over anhydrous Na2SO4 and concentrated. The crude product was purified by flash column chromatography using silica gel column using hexane:ethyl acetate as eluent to yield 15B (1.5 g, 75% yield). 1H NMR (CDCl3, 400 MHz) δ 8.05 (d, 1H), 7.5 (m, 1H), 7.3 (m, 1H), 7.2 (m, 1H), 3.67 (m, 1H), 3.3 (m, 1H), 3.14 (m, 1H), 1.3 (d, 3H). LCMS-(M+1)+ 162.

Workup

  1. additionISA (2 g) was added to the Eatons reagent
  2. temperatureThe reaction mixture was cooled to rt
  3. customquenched with ice
  4. extractionextracted with ethyl acetate
  5. washCombined organic layer was washed with 10% NaHCO3 solution (2×100 mL), water (1×100 mL), brine (1×100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-151ac4b5705f45a59f7f8081ddcde546
Source dataset
uspto-grants-2011_10
Patent number
US08039506B2

Reaction notes

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