Hydrochloric Acid → 2-(2-Methoxyphenoxy)benzoic acid

HRID 730065Notes

Reaction equation

HRID 730065 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25].Cl>C1(C)C=CC=CC=1.CC#N.CC#N.CC#N.CC#N.F[P-](F)(F)(F)(F)F.[Cu+].C(OCC)(=O)C>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 460GuaiacolHCID 69402-Bromobenzoic acidHCID 10796Cesium carbonate

Product 1

HCID 5786892-(2-Methoxyphenoxy)benzoic acidYield 982.6%

Reagents, catalysts & solvents 3

HCID 11068737tetrakis(acetonitrile)copper(I) hexafluorophosphateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrakis(acetonitrile)copper(I) hexafluorophosphate (4.62 g, 12.4 mmol), cesium carbonate (32 g, 98 mmol), 2-bromobenzoic acid (10g, 49. 7 mmol) and 2-methoxyphenol (6.17 g, 49.7 mmol) were combined in toluene (100 mL), and the mixture was heated to reflux for 15 hr. Ethyl acetate (200 mL) and 1N HCl (200 mL) were added, and the organic layer was separated. The organic layer was dried over MgSO4, filtered, and evaporated to yield 16.8 g of Compound 1a. The residue was used without further purification. MS m/z (M-H)− 243.1.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 15 hr
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7f2ea80a77f34fedaea6bd83d6e05700
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

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