Methyl 3-(bromomethyl)benzoate → Methyl 3-(methoxymethyl)benzoate

HRID 45225Notes

Reaction equation

HRID 45225 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[CH3:13][O-:14].[Na+].[Na]>CO>[CH3:13][O:14][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 23080888Methyl 3-(methoxymethyl)benzoateYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
65 °C

Procedure

To a solution of 15 g (65.5 mmol) of methyl 3-(bromomethyl)benzoate in 20 mL of anhydrous MeOH is added dropwise, at room temperature, a solution of sodium methoxide in MeOH, prepared beforehand from 2.25 g (98.2 mmol) of sodium in 65 mL of MeOH. The reaction medium is then heated for 4 hours at 65° C. and then concentrated under reduced pressure, taken up in 500 mL of DCM, washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. 7.8 g of methyl 3-(methoxymethyl)benzoate are obtained in the form of an oil, which is used without further purification in the following step.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7855b89aa4b542e5b6f1508136a802f1
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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