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

HRID 731973Notes

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+]>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

Conditions

Temperature: 80 °C

Procedure

This compound was prepared in a manner analogous to that set forth in Step E of Example 1, using 25.3 grams (0.086 mole) of 4-(2,6-dichloro-4-hydroxyphenoxy)butyl acetate, 19.5 grams (0.1 mole) of 1,1,1,3-tetrachloropropane, and 18 grams (0.13 mole) of potassium carbonate in 250 mL of DMF was heated at 80° C. during a 16 hour period. 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 27.1 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

customThis compound was prepared in a manner analogous to that set forth in Step E of Example 1
customThe crude reaction product
customwas purified with column chromatography on silica gel using 1:1 methylene chloride
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-265c5cc8f9d34d64afca28140fef18a4
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585891B2

Reaction notes

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