HCID 68727506, compound → HCID 68726788, compound

HRID 493204Notes

Reaction equation

HRID 493204 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[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:20])[CH:17]([CH3:19])[CH3:18])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:3][C:4](=[O:21])[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:20])[CH:17]([CH3:18])[CH3:19])[CH3:2]

Participants

4

Reactant 1

HCID 68727506HCID 68727506, compound

Product 1

HCID 68726788HCID 68726788, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
37.5 °C

Procedure

The above prepared [4-chloro-2-(1-hydroxy-2-methyl-propyl)-5-methoxy-phenoxy]-acetic acid ethyl ester (1.56 g, 4.92 mmol) was dissolved in 50 mL of CH2Cl2, treated with MnO2 (12.84 g, 30 eq.), and the reaction mixture vigorously stirred over night at 35-40° C. Cooling, filtration over a pad of Celite, copiously rinsing, and evaporation of the solvent, followed by flash chromatography (SiO2, heptane/AcOEt=72/28) and direct crystallization afforded 0.887 g of the title compound as off-white crystals.

Workup

  1. temperatureCooling
  2. filtrationfiltration over a pad of Celite
  3. washcopiously rinsing
  4. customevaporation of the solvent
  5. customfollowed by flash chromatography (SiO2, heptane/AcOEt=72/28) and direct crystallization

Sources & evidence

ORD record
ord-d81d2b9ded0b47128bbf72023fa73a3e
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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