HCID 68725817, compound → HCID 68726944, compound

HRID 493213Notes

Reaction equation

HRID 493213 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[CH:16]([OH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[C:16](=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH3:2]

Participants

4

Reactant 1

HCID 68725817HCID 68725817, compound

Product 1

HCID 68726944HCID 68726944, compoundYield 39.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

The above prepared [4-chloro-2-(hydroxy-phenyl-methyl)-5-methoxy-phenoxy]-acetic acid ethyl ester (1.91 g, 3.81 mmol, corrected for purity) was dissolved in 50 mL of CH2Cl2, treated with MnO2 (8.28 g, 25 eq.), and the reaction mixture vigorously stirred over night. Filtration over a pad of Celite, carefully rinsing, and evaporation of the solvent, followed by flash chromatography (SiO2, heptane/AcOEt=7/3) and crystallization from heptane/AcOEt gave 0.530 g of the title compound as white crystals.

Workup

  1. filtrationFiltration over a pad of Celite
  2. washcarefully rinsing
  3. customevaporation of the solvent
  4. customfollowed by flash chromatography (SiO2, heptane/AcOEt=7/3) and crystallization from heptane/AcOEt

Sources & evidence

ORD record
ord-da18aa714fcc47c9b3e04a7bd78aa76f
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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