Hydrochloric Acid → 2-(4-Methoxyphenyl)benzoic acid

HRID 1990779Notes

Reaction equation

HRID 1990779 reaction equation
C(OCC)C.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1.C1(=O)[O:21][C:19](=[O:20])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.Cl>O1CCCC1>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:17]2[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19]([OH:21])=[O:20])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6811Phthalic AnhydrideHCID 178491912HCID 178491912, compound

Product 1

HCID 2668302-(4-Methoxyphenyl)benzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 ml (0.11 mol) of a diethyl ether solution of 1 M 4-methoxyphenylmagnesium bromide was dropwise added to a tetrahydrofuran solution (200 ml) of 14.81 g (0.10 mol) of phthalic anhydride at −78° C., and stirred overnight at room temperature. Aqueous 1 N hydrochloric acid solution was added to the reaction liquid, extracted with chloroform, and the organic layer was washed with saturated saline water. This was dried with anhydrous sodium sulfate, then the reaction liquid was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=1/2) to obtain 25.63 g (yield: 100%) of 2-(4-methoxyphenyl)-benzoic acid as a yellow oily substance.

Workup

  1. extractionextracted with chloroform
  2. washthe organic layer was washed with saturated saline water
  3. dry with materialThis was dried with anhydrous sodium sulfate
  4. customthe reaction liquid
  5. concentrationwas concentrated under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-75b0e2bbec144cbda33d83466b679086
Source dataset
uspto-grants-2010_01
Patent number
US07645756B2

Reaction notes

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