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

HRID 1006696

Reaction equation

HRID 1006696 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-e427bd3518ee4354a3439f316ca9d241
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Linked notes

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