p-Toluenesulfonic acid monohydrate → HCID 13833842, compound

HRID 2191039Notes

Reaction equation

HRID 2191039 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@H:7]([OH:8])[C@@H:6]([OH:9])[CH:5]([O:10][CH3:11])[O:4]1.O.[C:13]1(C)[CH:18]=CC(S(O)(=O)=O)=C[CH:14]=1>CC(C)=O.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:11][O:10][CH:5]1[O:4][C@H:3]2[C@H:7]([O:8][C:13]([CH3:18])([CH3:14])[O:1][CH2:2]2)[C@H:6]1[OH:9]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11073752HCID 11073752, compound

Product 1

HCID 13833842HCID 13833842, compoundYield 5,030.4%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 180AcetoneSolvent

Procedure

Compound 35.2 (120.45 g, 734 mmol) was dissolved in 1.5 L acetone, treated with p-toluene sulfonic acid monohydrate (0.6 g, 3.15 mmol) and CuSO4 (225 g, 1.41 mol). The mixture was stirred for 60 h. The solid was removed by filtration and washed with (3×200 mL) acetone. The filtrate and the washings were combined and neutralized with 2.5 mL concentrated ammonium hydroxide. The solvent was removed by reduced pressure and the residue was dissolved in 750 mL CH2Cl2 and washed with 3'100 mL water. The water extracts were combined and extracted with 3×100 mL CH2Cl2. The CH2Cl2 extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 0-3% MeOH in CH2Cl2 to give compound 35.3 (32.36 g, 21.6% yield).

Workup

  1. customThe solid was removed by filtration
  2. washwashed with (3×200 mL) acetone
  3. customThe solvent was removed by reduced pressure
  4. dissolutionthe residue was dissolved in 750 mL CH2Cl2
  5. washwashed with 3'100 mL water
  6. extractionextracted with 3×100 mL CH2Cl2
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washeluting with 0-3% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-3e228bb20cb0433db4b8471beab2682b
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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