p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 896012Notes

Reaction equation

HRID 896012 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[CH3:12][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178418361HCID 178418361, compound

Product 1

HCID 6101p-Toluenesulfonic acidYield 162.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 5-nitro-3,4-dihydro-2H-benzo[1,4]oxazin-3-yl)-methanol (10.0 g, 47.6 mmole), p-toluenesulfonic acid monohydrate (19.0 g, 0.1 mole) and 1.0 g of 10% palladium on carbon in 250 mL of methanol was treated with 50 psi of hydrogen on a Parr shaker for 2 hours. The catalyst was filtered and washed with additional methanol. The solvent was evaporated in vacuum to yield 28 g of the p-toluenesulfonate of the title compound as a pink solid. This compound was used for the next step without further purification.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with additional methanol
  3. customThe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-0a417472ea0947e58978fbd2f0d738a3
Source dataset
uspto-grants-2005_07
Patent number
US06919334B2

Reaction notes

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