3-(Bromomethyl)benzaldehyde → 3-(Methoxymethyl)benzaldehyde

HRID 1770608Notes

Reaction equation

HRID 1770608 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].[CH3:11][O:12][Na]>CO>[CH3:11][O:12][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7]

Participants

4

Reactant 2

HCID 71278253-(Bromomethyl)benzaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 122456233-(Methoxymethyl)benzaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-(bromomethyl)benzaldehyde (1.00 g, 5.02 mmol) was dissolved in MeOH (100 mL) and treated with 0.5M solution of MeONa (5 equiv.) in MeOH. The mixture was stirred overnight at RT and MeOH was evaporated under reduced pressure. The residue was acidified to pH ˜6 with 1M aqueous HCl solution. DCM (100 mL) was added and the mixture was vigorously stirred overnight. The organic layer was separated, dried over Na2SO4 and the solvent was removed under reduce pressure to furnish the desired material as yellowish oil (560 mg, 3.75 mmol, 74%). 1H NMR (DMSO, 400 MHz): δ3.33 (s, 3H), 4.51 (s, 1H), 7.62 (m, 2H), 7.85 (m, 2H), 10.02 (s, 1H). MS 151 (MH1).

Workup

  1. customMeOH was evaporated under reduced pressure
  2. additionDCM (100 mL) was added
  3. waitthe mixture was vigorously stirred overnight
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-5e10d825fd674490bc0167706867cf4e
Source dataset
uspto-grants-2016_02
Patent number
US09247759B2

Reaction notes

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