Water → HCID 23332241, compound

HRID 2419160Notes

Reaction equation

HRID 2419160 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][OH:12])=[CH:7][CH:6]=1.S(OC)(O[CH3:25])(=O)=O.O>[OH-].[Na+]>[CH3:25][O:12][CH2:11][CH:10]([O:9][C:8]1[CH:14]=[CH:15][C:5]([O:4][C:3]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:2]=2[Cl:1])=[CH:6][CH:7]=1)[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6497Dimethyl SulfateHCID 12804883HCID 12804883, compound

Product 1

HCID 23332241HCID 23332241, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

6 g of β-[4-(2,4-dichlorophenoxy)phenoxy]propanol was dissolved in 3.4 g of 30% aqueous sodium hydroxide. The solution was heated at a temperature of 60° C, then 3.1 g of dimethyl sulfate was added dropwise to the solution with stirring and the mixture was allowed to react for 1.5 hours. 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, and the ether was removed by distillation. The residue was distilled under reduced pressure to obtain 3.0 g of the desired product having a boiling point of 182° to 185° C/1.5 mmHg.

Workup

  1. customto react for 1.5 hours
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe ether was removed by distillation
  6. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-e9f0bef0336844d3a11877a18e17dbd7
Source dataset
uspto-grants-1978_08
Patent number
US04105435

Reaction notes

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