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

HRID 731971Notes

Reaction equation

HRID 731971 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[OH:17].[C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)(=[O:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][O:17][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:4]=1[Cl:16])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 120841702,6-Dichloro-4-benzyloxyphenol

Product 1

HCID 578381394-[2,6-Dichloro-4-(phenylmethoxy)phenoxy]butyl acetateYield 92.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in a manner analogous to that set forth in Step B of Example 1, using 25 grams (0.093 mole) of 2,6-dichloro-4-phenylmethoxyphenol (known compound), 19.5 grams (0.10 mole) of 4-bromobutyl acetate and 19.4 grams (0.14 mole) of potassium carbonate in 400 mL of DMF, differing in that the reaction mixture was warmed to 80 C., where it was maintained prior to work-up. The crude reaction product was purified with column chromatography on silica gel using 1:1 methylene chloride:hexane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 33.1 grams of compound the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that set forth in Step B of Example 1
  2. temperaturewas warmed to 80 C
  3. temperature, where it was maintained
  4. customThe crude reaction product
  5. customwas purified with column chromatography on silica gel using 1:1 methylene chloride
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ffc1d0947084653a6c9133460df124f
Source dataset
uspto-grants-2009_09
Patent number
US07585891B2

Reaction notes

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