4-[2,6-Dichloro-4-(phenylmethoxy)phenoxy]butyl acetate → 4-(2,6-Dichloro-4-hydroxyphenoxy)butyl acetate

HRID 2234816Notes

Reaction equation

HRID 2234816 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([Cl:16])=[CH:14][C:13]([O:17]CC2C=CC=CC=2)=[CH:12][C:11]=1[Cl:25])(=[O:3])[CH3:2].[H][H]>[Pd].C(O)C>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([Cl:25])=[CH:12][C:13]([OH:17])=[CH:14][C:15]=1[Cl:16])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 578381394-[2,6-Dichloro-4-(phenylmethoxy)phenoxy]butyl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 578381414-(2,6-Dichloro-4-hydroxyphenoxy)butyl acetateYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 33.0 grams (0.086 mole) of 4-[2,6-dichloro-4-(phenylmethoxy)phenoxy]butyl acetate and 0.05 gram (catalyst) of 10% palladium on carbon in 350 mL of ethanol was subjected to hydrogenation conditions using a Parr hydrogenator. After the theoretical uptake of hydrogen, gas chromatographic (GC) analysis of the reaction mixture indicated the reaction was about 50% complete. Additional catalyst was added and the reaction mixture was again subjected to hydrogenation conditions using the Parr hydrogenator. GC analysis of the reaction mixture indicated the reaction was now complete. The reaction mixture was filtered and concentrated under reduced pressure, yielding 25.4 grams of the subject compound as a residue. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionAdditional catalyst was added
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89675b2277ec48c093283329b23c3610
Source dataset
uspto-grants-2010_05
Patent number
US07713970B2

Reaction notes

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