HCID 59205673, compound → HCID 59205674, compound

HRID 2242519Notes

Reaction equation

HRID 2242519 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([O:12]CC2C=CC=CC=2)[CH:9]=[C:8]([Cl:20])[C:3]=1[O:4][CH2:5][CH2:6][OH:7].[H][H]>[Pd].C(O)C>[Cl:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([Cl:20])[C:3]=1[O:4][CH2:5][CH2:6][OH:7]

Participants

5

Reactant 2

HCID 59205673HCID 59205673, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 59205674HCID 59205674, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

This compound was prepared in a manner analogous to that of Example 1 Step B, by the treatment of 16.0 grams (0.051 mole) of 2-[2,6-dichloro-4-(phenylmethoxy)phenoxy]ethan-1-ol with hydrogen gas in the presence of a catalytic amount of 10% palladium on carbon in about 400 mL of ethanol using a Parr hydrigenaton apparatus. Following the theoretical uptake of hydrogen, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 1:2 ethyl acetate:hexane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 10.5 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Example 1 Step B
  2. filtrationthe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure to a residue
  4. customThe residue was purified with column chromatography on silica gel using 1:2 ethyl acetate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-649b72d9679e48a3887b01db1e3d21cd
Source dataset
uspto-grants-2010_03
Patent number
US07671201B2

Reaction notes

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