Dichloromethane → 2-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)butan-1-one

HRID 565124Notes

Reaction equation

HRID 565124 reaction equation
[OH:1][C:2]([CH3:15])([CH2:13][CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8](SC)=[CH:7][CH:6]=1)=[O:4].O[O:17][S:18]([O-:20])=O.[K+].[CH2:22](Cl)Cl>CO.O>[OH:1][C:2]([CH3:15])([CH2:13][CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:18]([CH3:22])(=[O:20])=[O:17])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 101307312-Hydroxy-2-methyl-1-[4-(methylthio)phenyl]-1-butanoneHCID 23707502Potassium hydroxy sulfite2×

Product 1

HCID 154806442-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)butan-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the tertiary alcohol from Step 2 (4.5 g, 20.1 mmol) in CH2Cl2 (100 mL), MeOH (100 mL) and H2O (25 mL) was added Oxone® (9 g). After 3 h at r.t. a second 9 g portion of Oxone® was added and the mixture was stirred overnight at r.t. The solvent was then removed under vacuum, and the residue was partitioned between EtOAc and H2O. The organic phase was washed with H2O and brine, and was then dried (MgSO4), filtered, and evaporated. Purification was effected by flash chromatography (1:2 EtOAc: hexane) to give 5.5 g of the title compound as a tan coloured oil.

Workup

  1. customThe solvent was then removed under vacuum
  2. customthe residue was partitioned between EtOAc and H2O
  3. washThe organic phase was washed with H2O and brine
  4. dry with materialwas then dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification

Sources & evidence

ORD record
ord-c561e3f238024581b9ae7e19dc4819a5
Source dataset
uspto-grants-2001_01
Patent number
US06169188A

Reaction notes

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