Dimethyl Sulfate → HCID 19363464, compound

HRID 850413Notes

Reaction equation

HRID 850413 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[OH-].[Na+].S(OC)(O[CH3:23])(=O)=O>C(O)C>[CH3:23][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 6497Dimethyl Sulfate2×HCID 14798Sodium Hydroxide2×HCID 19363317HCID 19363317, compound

Product 1

HCID 19363464HCID 19363464, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

1-(2-Hydroxy-5-methylphenyl)heptan-1-one (127 g, 0.61 mol), a 2.5N aqueous sodium hydroxide solution (250 ml) and ethanol (250 ml) were mixed, and this solution was cooled to 0° C. Dimethyl sulfate (60 ml) was added, and the mixture was refluxed under heating for 2 hours. Dimethyl sulfate (40 ml) and a 2.5N aqueous sodium hydroxide solution (170 ml) were further added, and the mixture was refluxed under heating for 2 hours. The reaction mature was concentrated under reduced pressure and the obtained residue was extracted twice with ether (200 ml). The organic layers were combined, washed twice with a 2.5N aqueous sodium hydroxide solution and saturated brine (100 ml1 each), and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (n-hexane/ethyl acetate=95/5) to give 1-(2-methoxy-5-methylphenyl)heptan-1-one (82 g, 57%) as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating for 2 hours
  5. customThe reaction
  6. concentrationmature was concentrated under reduced pressure
  7. extractionthe obtained residue was extracted twice with ether (200 ml)
  8. washwashed twice with a 2.5N aqueous sodium hydroxide solution and saturated brine (100 ml1 each), and
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe drying agent was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe obtained residue was purified by column chromatography (n-hexane/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-d4544d03442f49b99bc32c0f3333e570
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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