Hydrochloric Acid → 2-Hydroxy-4'(methylthio)isobutyrophenone

HRID 1602515Notes

Reaction equation

HRID 1602515 reaction equation
[CH3:1][CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].C(Cl)(Cl)(Cl)Cl.[OH-:19].[Na+].Cl>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1.O.[Cl-].[Na+].O.CCOC(C)=O>[OH:19][C:2]([CH3:13])([CH3:1])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([S:11][CH3:12])=[CH:9][CH:10]=1)=[O:4]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 5943Carbon TetrachlorideHCID 14798Sodium HydroxideHCID 8525392-Methyl-1-[4-(methylthio)phenyl]-1-propanone

Product 1

HCID 114131682-Hydroxy-4'(methylthio)isobutyrophenone

Reagents, catalysts & solvents 5

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-methyl-1-(4-(methylthio)phenyl)propan-1-one (28.5 g, 147 mmol, Step 1), Aliquat 336 (11.0 mL, 24 mmol) and carbon tetrachloride (21 mL, 218 mmol) in toluene (43 mL) was added sodium hydroxide (12.9 g, pellets, 322 mmol). The reaction was stirred at 15° C. for 2h and then at r.t. for 16h. The reaction was diluted with water (100 mL), brine (100 mL) and EtOAc (300 mL). The aqueous phase was acidified with 1 N HCl and extracted with EtOAc (100 mL). The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by silica gel chromatography eluted with 15% EtOAc in hexane to give the title compound as a thick syrup.

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography
  5. washeluted with 15% EtOAc in hexane

Sources & evidence

ORD record
ord-a8cba86aaf01477c90fe17093b047053
Source dataset
uspto-grants-1999_11
Patent number
US05981576

Reaction notes

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