Water → (3-Methoxy-5-methylphenyl)methanol

HRID 709721Notes

Reaction equation

HRID 709721 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[CH:4]=1.C(=O)([O-])[OH:13].[Na+].O>CC(C)=O>[CH3:11][O:10][C:5]1[CH:4]=[C:3]([CH2:2][OH:13])[CH:8]=[C:7]([CH3:9])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 5855341-(Bromomethyl)-3-methoxy-5-methylbenzene

Product 1

HCID 11030016(3-Methoxy-5-methylphenyl)methanolYield 80.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-(bromomethyl)-3-methoxy-5-methylbenzene (2.14 g) in acetone (80 mL) were added sodium hydrogen carbonate (1.05 g) and water (50 mL), and the mixture was heated under reflux for 18 hr. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.22 g) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hr
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cb45ff73b9a34a3c921d4b4483304c8b
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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