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

HRID 2234815Notes

Reaction equation

HRID 2234815 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+].[Cl-].[Na+]>CN(C=O)C.O>[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

7

Reactant 4

HCID 5234Sodium ChlorideHCID 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 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, a solution of 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 was stirred at ambient temperature for two hours, then it was heated to 80° C. where it was maintained during a 20 hour period. After this time the reaction mixture was allowed to cool to ambient temperature where it stirred during an additional 20 hour period. The reaction mixture was then stirred with 400 mL of water, saturated with sodium chloride and extracted with four 150 mL portions of diethyl ether. The combined extracts were washed with two 150 mL portions of water, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The crude residue 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. temperaturewas maintained during a 20 hour period
  2. temperatureto cool to ambient temperature where it
  3. extractionextracted with four 150 mL portions of diethyl ether
  4. washThe combined extracts were washed with two 150 mL portions of water
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. customThe crude residue was purified with column chromatography on silica gel using 1:1 methylene chloride
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7bed74e8276d44ab9d3fa83fcf7b1fd5
Source dataset
uspto-grants-2010_05
Patent number
US07713970B2

Reaction notes

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