Diethyl Sulfate → (2-Ethoxyethoxy)benzene

HRID 1463174Notes

Reaction equation

HRID 1463174 reaction equation
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][CH2:12][O-].[Na+].O1CCOCC1.S(OCC)(OCC)(=O)=O>O>[O:1]([CH2:8][CH2:9][O:10][CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6163Diethyl SulfateHCID 31236PhenoxyethanolHCID 312751,4-DioxaneHCID 2723922Sodium ethoxide

Product 1

HCID 542463(2-Ethoxyethoxy)benzeneYield 92.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

143.0 g (1.04 mol) of 2-phenoxyethanol, 81.0 g (1.19 mol) of sodium ethylate and 291 g of 1,4-dioxane are placed in a 1-liter four-necked flask equipped with a stirrer, a thermometer, a distillating column and a nitrogen-inlet tube. The solution is heated to 90° to 105° C., and then 200 g of the solvent is removed in a period of 2 hours. The distillating column is then replaced by a dropping funnel, and 183.5 g (1.19 mol) of diethyl sulfate is added thereto dropwise at 45° C. over a period of 30 minutes. After stirring the reaction mixture at 60° C. for 1 hour, the reaction product is placed in water and extracted with ether. The solvent is removed using an evaporator, and further distilled under reduced pressure to yield 160 g of ethyl 2-phenoxyethyl ether.

Workup

  1. customequipped with a stirrer
  2. temperatureThe solution is heated to 90° to 105° C.
  3. custom200 g of the solvent is removed in a period of 2 hours
  4. customThe distillating column is then replaced by a dropping funnel
  5. extractionextracted with ether
  6. customThe solvent is removed
  7. customan evaporator
  8. distillationfurther distilled under reduced pressure

Sources & evidence

ORD record
ord-54cde9ce25474769a8c3ecf193c18682
Source dataset
uspto-grants-1994_04
Patent number
US05300245

Reaction notes

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