Methanol → Methyl 2-(4-Bromophenoxymethyl)benzoic Acid

HRID 1515223Notes

Reaction equation

HRID 1515223 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([O:14]C)=[O:13])=[CH:6][CH:5]=1.[CH3:22]O>>[CH3:22][C:19]1[C:10]([CH2:9][O:8][C:7]2[CH:20]=[CH:21][C:4]([Br:3])=[CH:5][CH:6]=2)=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 53995976Methyl 2-((4-bromophenoxy)methyl)benzoate

Product 1

HCID 68526746Methyl 2-(4-Bromophenoxymethyl)benzoic AcidYield 84%

Procedure

A 2 mol/L aqueous sodium hydroxide solution (250 mL) was added to a methanol (1 L) solution of methyl 2-(4-bromophenoxymethyl)-benzoate (139 g, 432 mmol), and the mixture was stirred overnight while heating under reflux. Methanol was distilled off under a reduced pressure, and a 6 mol/L hydrochloric acid was added to the residue obtained to precipitate the crystals, and the precipitated crystals were collected by filtration, and sufficiently washed with water. The crystals were dried over phosphorus pentoxide at 50° C., to give 112 g (84%) of the captioned compound.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. distillationMethanol was distilled off under a reduced pressure
  4. additiona 6 mol/L hydrochloric acid was added to the residue
  5. customobtained
  6. customto precipitate the crystals
  7. filtrationthe precipitated crystals were collected by filtration
  8. washsufficiently washed with water
  9. dry with materialThe crystals were dried over phosphorus pentoxide at 50° C.

Sources & evidence

ORD record
ord-d032d885cf694bdf85fbc0952f03b1c6
Source dataset
uspto-grants-2012_07
Patent number
US08222419B2

Reaction notes

Loading…