Sodium Methoxide → Methyl 3-methoxy-2-methoxymethylbenzoate

HRID 512770Notes

Reaction equation

HRID 512770 reaction equation
Br[CH2:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[CH3:15][O-:16].[Na+]>CO>[CH3:14][O:13][C:12]1[C:3]([CH2:2][O:16][CH3:15])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 12527050Methyl 2-(bromomethyl)-3-methoxybenzoate

Product 1

HCID 59838621Methyl 3-methoxy-2-methoxymethylbenzoateYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 100 mL flask containing 10.1 g (0.039 mol) of methyl 2-bromomethyl-3-methoxybenzoate in 50 mL of CH3OH, were added 19 g of a 25% wt. solution of NaOMe (4.74 g, 0.087 mol). The reaction was stirred at room temperature for 2 hours and then evaporated on a rotary evaporator to remove the CH3OH. About 200 mL of water were added to the residue and the resulting solution was extracted with CHCl3. The CHCl3 extract was dried and evaporated to yield 6.27 g of crude methyl 3-methoxy-2-methoxymethylbenzoate (77% yield). 1H NMR (CDCl3, 300 MHz) δ (ppm): 7-7.4 (multiple, 3H), 4.783 (s, 2H), 3.897 (s, 3H), 3.864 (s, 3H), 3.37 (s, 3H). 6.27 g of methyl 3-methoxy-2-methoxymethylbenzoate was stirred with a 20% aqueous KOH solution (6.7 g, 0.12 mol in 34 g of solution) at 50° C. in an oil bath for 4-5 hours, and then at room temperature for 16 hours. The reaction mixture was acidified with 3N HCl to pH 2 and extracted with CH2Cl2. The CH2Cl2 extract was dried and evaporated to yield 5.35 g of 3-methoxy-2-methoxymethylbenzoic acid (92% yield). 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.65 (1H, d), 7.40 (t, 1H), 7.10 (d, 1H), 4.83 (s, 2H), 3.88 (s, 3H), 3.46 (s, 3H).

Workup

  1. customevaporated on a rotary evaporator
  2. customto remove the CH3OH
  3. additionAbout 200 mL of water were added to the residue
  4. extractionthe resulting solution was extracted with CHCl3
  5. extractionThe CHCl3 extract
  6. customwas dried
  7. customevaporated

Sources & evidence

ORD record
ord-506eb00123764cc089ff021b35fbf9fa
Source dataset
uspto-grants-2015_08
Patent number
US09102648B1

Reaction notes

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