4-(Bromomethyl)phenylacetic acid → 4-(Methoxymethyl)phenylacetic acid

HRID 987137Notes

Reaction equation

HRID 987137 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[CH3:13][O-:14].[Na+]>CO>[CH3:13][O:14][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 45190564-(Bromomethyl)phenylacetic acidHCID 10942334Sodium Methoxide

Product 1

HCID 229884284-(Methoxymethyl)phenylacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(Bromomethyl)phenylacetic acid (4.85 g, 21.17 mmole), sodium methoxide (30% in methanol, ˜12 ml, ˜65 mmole)) and methanol (30 ml) were mixed and refluxed over night. The reaction mixture was allowed to cool down and was then acidified with HCL (1M). Methanol was evaporated. Water was added and the reaction mixture was extracted three times with dichloromethane. The combined organic phases was washed with brine and dried with NA2SO4. Evaporation gave 3.6 g, 94.4%, of the desired product.

Workup

  1. temperaturerefluxed over night
  2. temperatureto cool down
  3. customMethanol was evaporated
  4. additionWater was added
  5. extractionthe reaction mixture was extracted three times with dichloromethane
  6. washThe combined organic phases was washed with brine
  7. customdried with NA2SO4
  8. customEvaporation
  9. customgave 3.6 g, 94.4%

Sources & evidence

ORD record
ord-bd283f686f29467583e9f897bb4d2411
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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