Phthalic Anhydride → 2-(2-Methoxybenzoyl)benzoic acid

HRID 396584Notes

Reaction equation

HRID 396584 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[C:11]1(=[O:21])[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[Cl-].[NH4+]>O1CCCC1>[CH3:10][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:11]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])=[O:21]

Participants

6

Reactant 4

HCID 6811Phthalic AnhydrideHCID 113582-BromoanisoleHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 3340732-(2-Methoxybenzoyl)benzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution in tetrahydrofuran (17 ml) of a Grignard's reagent prepared from magnesium (120 mg, 5.1 mmol) and 2-bromoanisole (0.55 ml, 4.4 mmol) was added dropwise to a solution of phthalic anhydride (500 mg, 3.4 mmol) in tetrahydrofuran (12 ml) in an atmosphere of nitrogen at −70° C. over a period of 10 minutes. The reaction mixture was stirred at −70° C. for 2.5 hours, and aqueous saturated ammonium chloride solution was added. The mixture was extracted with ethyl acetate, and the organic layer was washed with aqueous saturated sodium chloride solution, dried and concentrated under reduced pressure to obtain crude 2-(2-methoxybenzoyl)benzoic acid (770 mg, yield: 90%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with aqueous saturated sodium chloride solution
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fcadd6ffa5d44210a7d0b684504f1432
Source dataset
uspto-grants-2003_08
Patent number
US06608098B1

Reaction notes

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