HCID 19045363, compound → HCID 19045221, compound

HRID 1591197Notes

Reaction equation

HRID 1591197 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9][CH3:10])=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].I([O-])(=O)(=O)=[O:15].[Na+]>CO.O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH3:10])=[O:15])=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 19045363HCID 19045363, compoundHCID 23667635Sodium periodate

Product 1

HCID 19045221HCID 19045221, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2'-hydroxy-5'-(methylthiomethyl)acetophenone (2.20 g, 11.0 mmol) in 70 mL MeOH cooled in an ice bath was added a solution of sodium metaperiodate (2.49 g, 12.1 mmol) in 115 mL water. The resulting cloudy mixture was stirred two hours with cooling then partially concentrated in vacuo to remove methanol. The remaining aqueous mixture was extracted with chloroform (3×125 mL). The extract was washed with 50 mL water and brine, dried over sodium sulfate, and filtered. The filtrate was concentrated in vacuo to give crude product which was recrystallized from n-butylchloride to give 1.39 g (60%) product, as a pale yellow solid, mp 95°-97° C.

Workup

  1. temperaturewith cooling
  2. concentrationthen partially concentrated in vacuo
  3. customto remove methanol
  4. extractionThe remaining aqueous mixture was extracted with chloroform (3×125 mL)
  5. washThe extract was washed with 50 mL water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give crude product which
  10. customwas recrystallized from n-butylchloride

Sources & evidence

ORD record
ord-76329e1b1dbb4ba6acab09128f1ce8ee
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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