Water → 4-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]butyl acetate

HRID 2234817Notes

Reaction equation

HRID 2234817 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]([OH:17])=[CH:12][C:11]=1[Cl:18])(=[O:3])[CH3:2].[Cl:19][C:20](Cl)([Cl:24])[CH2:21][CH2:22]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([Cl:18])=[CH:12][C:13]([O:17][CH2:22][CH:21]=[C:20]([Cl:24])[Cl:19])=[CH:14][C:15]=1[Cl:16])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 140561,1,1,3-TetrachloropropaneHCID 578381414-(2,6-Dichloro-4-hydroxyphenoxy)butyl acetate

Product 1

HCID 184295004-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]butyl acetateYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 25.3 grams (0.086 mole) of 4-(2,6-dichloro-4-hydroxyphenoxy)butyl acetate in 250 mL of DMF was stirred, and 19.5 grams (0.1 mole) of 1,1,1,3-tetrachloropropane was added, followed by 18 grams (0.13 mole) of potassium carbonate. Upon completion of addition the reaction mixture was heated at 80° C. during a 17 hour period. After this time the reaction mixture was cooled to ambient temperature, stirred with 350 mL of water and extracted with four 150 mL portions of diethyl ether. The combined extracts were washed with two 100 mL portions of water, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The 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 27.1 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperatureAfter this time the reaction mixture was cooled to ambient temperature
  3. extractionextracted with four 150 mL portions of diethyl ether
  4. washThe combined extracts were washed with two 100 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 residue was purified with column chromatography on silica gel using 1:1 methylene chloride
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-62c566b93eea487293e5af09845f56a3
Source dataset
uspto-grants-2010_05
Patent number
US07713970B2

Reaction notes

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