Methanol → 3-(methoxymethyl)benzoic Acid

HRID 980462Notes

Reaction equation

HRID 980462 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[CH3:12][OH:13]>C[O-].[Na+]>[CH3:12][O:13][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 887MethanolHCID 2456503-(Bromomethyl)benzoic acid

Product 1

HCID 49623543-(methoxymethyl)benzoic AcidYield 92%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

12 g (55.75 millimoles) of 3-bromomethyl-benzoic acid are dissolved in 10 ml of anhydrous methanol and to the solution 22.30 ml of sodium methylate (concentration 5 millimoles/ml) are added dropwise at room temperature. The reaction mixture is stirred for 5-10 minutes, the methanol is removed in vacuo. The residue is dissolved in 10 ml of ethyl acetate, to the solution 2 ml of water are added and the pH of the mixture is adjusted to 2-3 with a 2N sodium hydrogen sulfate solution at 0° C. The layers are separated, the organic phase is dried, filtered and the solvent is distilled off in vacuo. Thus 8.55 g of the title compound are obtained, yield 92,3%.

Workup

  1. additionare added dropwise at room temperature
  2. customthe methanol is removed in vacuo
  3. dissolutionThe residue is dissolved in 10 ml of ethyl acetate, to the solution 2 ml of water
  4. additionare added
  5. customis adjusted to 2-3 with a 2N sodium hydrogen sulfate solution at 0° C
  6. customThe layers are separated
  7. customthe organic phase is dried
  8. filtrationfiltered
  9. distillationthe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-adc8b7794f1e4a2488898ebc3ce61137
Source dataset
uspto-grants-1987_01
Patent number
US04638002

Reaction notes

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