Triethylamine → 2,4-Dichlorophenoxyethyl 2-[4-(3,5-dichloropyridin-2-yl-oxy)phenoxy]propanoate

HRID 977894Notes

Reaction equation

HRID 977894 reaction equation
[Cl:1][C:2]1[C:3]([O:9][C:10]2[CH:21]=[CH:20][C:13]([O:14][CH:15]([CH3:19])[C:16](Cl)=[O:17])=[CH:12][CH:11]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N([CH2:27][CH3:28])CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:9][C:10]2[CH:21]=[CH:20][C:13]([O:14][CH:15]([CH3:19])[C:16]([O:14][CH2:15][CH2:16][O:17][C:28]3[CH:27]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=3[Cl:8])=[O:17])=[CH:12][CH:11]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 131894782-{4-[(3,5-Dichloropyridin-2-yl)oxy]phenoxy}propanoyl chloride

Product 1

HCID 537105552,4-Dichlorophenoxyethyl 2-[4-(3,5-dichloropyridin-2-yl-oxy)phenoxy]propanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 2-[4-(3,5-dichloropyridin-2-yloxy)phenoxy]propanoic acid chloride (3.12 grams; 0.009 mol); triethylamine (5 ml): 2,4-dichlorophenoxyethethanol (1.94 grams; 0.0094 mol) and toluene (100 ml) were stirred in a glass reaction flask until thin layer chromatographic analysis showed completion of the reaction. This mixture was transferred to a separatory funnel and washed three times with water (70 ml). The washed material was dried and stripped to a yellow/brown gum (4.8 grams) that solidified on standing and was recrystallized from a mixture of methylene chloride and hexane. The first crop (1.5 grams) analyzed by elemental analysis as follows:

Workup

  1. customcompletion of the reaction
  2. customThis mixture was transferred to a separatory funnel
  3. washwashed three times with water (70 ml)
  4. customThe washed material was dried
  5. customwas recrystallized from a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-7301bd6a570e4df581b202c8434fe6f7
Source dataset
uspto-grants-1987_05
Patent number
US04662934

Reaction notes

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