Acetic Acid → 2-Bromo-1-methoxymethyl-3-methylbenzene

HRID 1369592

Reaction equation

HRID 1369592 reaction equation
[Br:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[C:11](=O)(O)[O-:12].[Na+].C(O)(=O)C>CO>[Br:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:12][CH3:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 109343202-Bromo-1-(bromomethyl)-3-methylbenzene

Product 1

HCID 138434542-Bromo-1-methoxymethyl-3-methylbenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-bromo-3-methylbenzylbromide (5.2 g, 0.0197 mol) in methanol (30 ml) was added saturated sodiumbicarbonate (5 ml) and the mixture was refluxed overnight. The mixture was neutralised with acetic acid and the solvent was evaporated under reduced pressure. Chromatography of the residue on silica gel using hexane:methylene chloride (7/3) as eluent gave 4.2 g (99%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-71cb6ed385944d218490145813e7eb64
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Linked notes

Loading…