Water → HCID 12804956, compound

HRID 224222Notes

Reaction equation

HRID 224222 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:15]=[CH:14][C:8]([O:9][CH:10]([CH3:13])[CH2:11]O)=[CH:7][CH:6]=1.N1C=CC=CC=1.S(Cl)([Cl:29])=O.O>C(OCC)C>[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:15]=[CH:14][C:8]([O:9][CH:10]([CH3:13])[CH2:11][Cl:29])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 12804883HCID 12804883, compound

Product 1

HCID 12804956HCID 12804956, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.0 g of β-[4-(2,4-Dichlorophenoxy)phenoxy]propanol and 1.1 g of pyridine were dissolved in 50 ml of anhydrous diethyl ether, and 1.5 g of thionyl chloride was added dropwise to the solution while cooling. The mixture was then heated for 1 hour while refluxing. The reaction mixture was poured into an appropriate amount of water, and the mixture was extracted with diethyl ether. The extract was washed with water and dried over anhydrous sodium sulfate. The ether was removed by distillation and the residue was distilled under reduced pressure to obtain 2.5 g of the desired product having a boiling point of 192° to 194° C./2 mmHg.

Workup

  1. temperaturewhile cooling
  2. temperatureThe mixture was then heated for 1 hour
  3. temperaturewhile refluxing
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe ether was removed by distillation
  8. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-983defbd0fa54814abd48cc954db4955
Source dataset
uspto-grants-1980_11
Patent number
US04231787

Reaction notes

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