4-(4-Methoxy-3-methylphenyl)butan-1-ol → 4-Methoxy-3-methylbenzenebutanoic acid

HRID 499012Notes

Reaction equation

HRID 499012 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[CH:5][C:4]=1[CH3:14].CC(C)=[O:17].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.C(O)(C)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:17])=[O:13])=[CH:5][C:4]=1[CH3:14]

Participants

5

Reactant 2

HCID 282961584-(4-Methoxy-3-methylphenyl)butan-1-olHCID 131709961Jones' reagent

Product 1

HCID 8057164-Methoxy-3-methylbenzenebutanoic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 1.7 grams (0.009 mole) of 4-(4-methoxy-3-methylphenyl)butan-1-ol in 50 mL of acetone was cooled to 0° C.-4° C., and about 15 to 20 mL (excess) of Jones Reagent was added dropwise. Upon completion of addition, the reaction mixture was stirred at 0° C. for two hours, then it was allowed to warm to ambient temperature, where it stirred for an additional three hours. After this time, the reaction mixture was diluted with isopropanol and filtered. The filter cake was washed with acetone, and the combined filtrate and wash were concentrated under reduced pressure to a residue. The residue was partitioned with methylene chloride and water and the separated organic layer was washed with water. The organic layer was then dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was dried under vacuum, yielding 1.1 grams of subject compound. The NMR spectrum was consistent with the proposed structure. The reaction was repeated to obtain an additional amount of subject compound.

Workup

  1. additionUpon completion of addition
  2. temperatureto warm to ambient temperature
  3. stirringwhere it stirred for an additional three hours
  4. filtrationfiltered
  5. washThe filter cake was washed with acetone
  6. washthe combined filtrate and wash
  7. concentrationwere concentrated under reduced pressure to a residue
  8. customThe residue was partitioned with methylene chloride and water
  9. washthe separated organic layer was washed with water
  10. dry with materialThe organic layer was then dried with sodium sulfate
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated under reduced pressure to a residue
  13. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-4df5d18468494f059b509f2a47aecd9c
Source dataset
uspto-grants-2010_08
Patent number
US07767667B2

Reaction notes

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