Potassium Carbonate → 4-{2,6-Dichloro-4-[(3,3-dichloroprop-2-EN-1-YL)oxy]phenoxy}butan-1-OL

HRID 1611457Notes

Reaction equation

HRID 1611457 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:15])[CH:5]=[C:6]([Cl:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[Cl:16][C:17](Cl)([Cl:21])[CH2:18][CH2:19]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:16][C:17]([Cl:21])=[CH:18][CH2:19][O:15][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[C:6]([Cl:14])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 140561,1,1,3-TetrachloropropaneHCID 222571313,5-Dichloro-4-(4-hydroxybutoxy)phenol

Product 1

HCID 222571304-{2,6-Dichloro-4-[(3,3-dichloroprop-2-EN-1-YL)oxy]phenoxy}butan-1-OLYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in a manner analogous to that of Step D of Example 1, using 9.3 grams (0.036 mole) of 3,5-dichloro-4-(4-hydroxybutoxy)phenol, 7.7 grams (0.042 mole) of 1,1,1,3-tetrachloropropane and 11.7 grams (0.080 mole) of potassium carbonate in 300 mL of DMF. The crude product was purified with column chromatography on silica gel using mixtures of 1:4 and 1:1 ethyl acetate and hexane as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 8.0 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step D of Example 1
  2. customThe crude product was purified with column chromatography on silica gel using mixtures of 1:4 and 1:1 ethyl acetate and hexane as eluants
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c6c271c56bf415e95f6318cb100f9e8
Source dataset
uspto-grants-2006_01
Patent number
US06987194B2

Reaction notes

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