2-(3-(Bromomethyl)phenyl)acetic acid → 2-[3-(Methoxymethyl)phenyl]acetic acid

HRID 990909Notes

Reaction equation

HRID 990909 reaction equation
[CH3:1][O-:2].[Na+].Br[CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1>CO>[CH3:1][O:2][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 103765092-(3-(Bromomethyl)phenyl)acetic acidHCID 10942334Sodium Methoxide

Product 1

HCID 184171202-[3-(Methoxymethyl)phenyl]acetic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under an atmosphere of argon gas, to sodium methoxide (160 g), methanol (800 ml) was added with stirring. Thereto, a solution of 3-bromomethylphenylacetic acid (226 g; prepared in Reference Example 18) in methanol (3200 ml) was added. The mixture was refluxed for 20 minutes. After the temperature of mixture became to room temperature, methanol was distilled off. The residue was poured into 2N HCl. Thereto, ethyl acetate was added. The organic layer was washed by an aqueous saturated solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated to obtain the title compound (176.3 g).

Workup

  1. temperatureThe mixture was refluxed for 20 minutes
  2. custombecame to room temperature
  3. distillationmethanol was distilled off
  4. additionThe residue was poured into 2N HCl
  5. additionThereto, ethyl acetate was added
  6. washThe organic layer was washed by an aqueous saturated solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2ae0d779930c46fa8960c5f985a142f4
Source dataset
uspto-grants-2002_10
Patent number
US06462081B1

Reaction notes

Loading…