Dimethyl Sulfate → 3-Methoxy-2-methylphenol

HRID 561918Notes

Reaction equation

HRID 561918 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:5]=1[OH:6].[CH3:12]OS(OC)(=O)=O>O>[CH3:12][O:6][C:5]1[C:4]([CH3:3])=[C:10]([OH:11])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 118432-MethylresorcinolHCID 14798Sodium Hydroxide2×

Product 1

HCID 2489133-Methoxy-2-methylphenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

3-Methoxy-2-methyl-phenol was prepared according to published procedure: J. Org. Chem. 55, 5, 1990, 1469. To a solution of 2.0 g (50 mmol) NaOH and 2-methylresorcinol (6.2 g, 50 mmol) in water (50 mL), dimethylsulfate (4.8 mL, 50 mmol) was added at 95° C. over 30 min, then reaction was stirred for 2 h at 95° C. After cooling to RT, the reaction mixture was poured into aqueous NaOH (8.0 g in 200 ml H2O). Extracted with Et2O (2×100 mL). The aqueous phase was acidified with 5 N aq. HCl, extracted with Et2O (2×100 mL), extracts were dried over Na2SO4 and evaporated. The residue was purified on SiO2 (200 g) column, hexane—EtOAc (0 to 20%). Yield 3.37 g (24.0 mmol, 49%), colorless oil.

Workup

  1. customreaction
  2. temperatureAfter cooling to RT
  3. extractionExtracted with Et2O (2×100 mL)
  4. extractionextracted with Et2O (2×100 mL), extracts
  5. dry with materialwere dried over Na2SO4
  6. customevaporated
  7. customThe residue was purified on SiO2 (200 g) column, hexane—EtOAc (0 to 20%)

Sources & evidence

ORD record
ord-f0d60b04f5f54a70a9cd85e4802df7cf
Source dataset
uspto-grants-2011_11
Patent number
US08063225B2

Reaction notes

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