Potassium Carbonate → Tert-butyl 2-(4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy)acetate

HRID 908655Notes

Reaction equation

HRID 908655 reaction equation
[Cl:1][C:2]([Cl:15])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([OH:13])=[C:8]([Cl:14])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>CN(C=O)C.O>[Cl:15][C:2]([Cl:1])=[CH:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([Cl:14])[C:9]([O:13][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[C:10]([Cl:12])[CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 59366522Tert-butyl 2-(4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy)acetateYield 102.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 0.5 gram (0.0017 mole) of 4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenol (known compound), 0.26 gram (0.0019 mole) of potassium carbonate and 0.26 gram (0.0017 mole) of tert-butyl chloroacetate in 0.12 mL of DMF was heated to 70° C. where it stirred for about 18 hours. After this time the reaction mixture was allowed to cool to ambient temperature. The reaction mixture was diluted with 30 mL of water then extracted with three 30 mL portions of ethyl acetate. The combined extracts were dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a yellow oil. The crude oil was purified with column chromatography on silica gel using a mixture of hexanes and ethyl acetate (93:7) as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.7 gram of the subject compound.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionthen extracted with three 30 mL portions of ethyl acetate
  3. dry with materialThe combined extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a yellow oil
  6. customThe crude oil was purified with column chromatography on silica gel using
  7. additiona mixture of hexanes and ethyl acetate (93:7) as an eluant
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2707f5d9892d4c47828c816ebcb3fbc2
Source dataset
uspto-grants-2011_09
Patent number
US08017635B2

Reaction notes

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