Sodium Hydroxide → 2-Hydroxy-2-methyl-1-[4-(methylthio)phenyl]-1-butanone

HRID 367363

Reaction equation

HRID 367363 reaction equation
[CH3:1][CH:2]([CH2:13][CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].[OH-:15].[Na+]>C1(C)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.Cl.[NH4+].[Cl-]>[OH:15][C:2]([CH3:1])([CH2:13][CH3:14])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([S:11][CH3:12])=[CH:9][CH:10]=1)=[O:4]

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 154806432-Methyl-1-[4-(methylthio)phenyl]-1-butanone

Product 1

HCID 101307312-Hydroxy-2-methyl-1-[4-(methylthio)phenyl]-1-butanone

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 5943Carbon TetrachlorideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of the ketone from step 1 (33 g) in toluene (48 mL), CCl4 (23.5 mL) and Aliquat, 336 (10.5 mL), was added NaOH pellets (14.5 g) and the resulting mixture was vigorously stirred for 2 days. The reaction mixture was diluted with 5N HCl, aqueous NH4Cl and extracted with Et2O. The organic layer was dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography eluted with EtOAc/Hexane 9% to give a yellow syrup.

Workup

  1. extractionextracted with Et2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography
  5. washeluted with EtOAc/Hexane 9%
  6. customto give a yellow syrup

Sources & evidence

ORD record
ord-311f7a1abbbf468b94f4f1a55dd01342
Source dataset
uspto-grants-2000_10
Patent number
US06133292

Linked notes

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