Acetonitrile → [4-Chloro-2-(2-methoxybenzoyl)phenyl]acetic acid

HRID 1444826Notes

Reaction equation

HRID 1444826 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)CC=1.C(#N)C.I([O-])(=O)(=O)=[O:23].[Na+].F[C:29](F)(F)[C:30]([OH:32])=[O:31]>O.[Ru](Cl)(Cl)Cl.O.CCCCCC>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:29][C:30]([OH:32])=[O:31])=[C:17]([C:9](=[O:23])[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:16]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 23667635Sodium periodateHCID 590255162-(5-Chloro-1H-inden-3-yl)phenyl methyl ether

Product 1

HCID 59025499[4-Chloro-2-(2-methoxybenzoyl)phenyl]acetic acid

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

12.02 g of the compound from Example 17A (44.76 mol) are mixed with 120 ml of acetonitrile, 120 ml of hexane and 180 ml of water. 39.25 g of sodium periodate (183.51 mol) and 0.18 g of ruthenium(III) chloride hydrate (0.81 mol) are added, and the mixture is stirred at room temperature for 48 h. For working up, the reaction mixture is acidified with a 5% aqueous trifluoroacetic acid solution and extracted three times with methylene chloride. The combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulphate, and the solvent is removed in a rotary evaporator. The residue is taken up in ethyl acetate, and the solution is stored at 5° C. for 16 h. The deposited crystals are filtered off and dried under high vacuum. 5.12 g (38% of theory) of the title compound are obtained.

Workup

  1. extractionextracted three times with methylene chloride
  2. washThe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed in a rotary evaporator
  5. waitthe solution is stored at 5° C. for 16 h
  6. filtrationThe deposited crystals are filtered off
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-2c6112d1afd44a3aaf3b715608feb35d
Source dataset
uspto-grants-2010_02
Patent number
US07662956B2

Reaction notes

Loading…