Reaction #41179

Reaction equation

hydrazine monohydrate

1-(2-bromoethoxy)-2-methoxyethane

→

[2-(2-methoxyethoxy)-ethyl]-hydrazine

Yield 85.0%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperatureheated to 40° C. in a preheated oil bath for 12 hours
2. 2
   TemperatureThe reaction was then cooled to room temperature
3. 3
   Concentrationconcentrated
4. 4
   Otherto remove the ethanol
5. 5
   ExtractionThe remaining aqueous layer was extracted with methylene chloride (2×100 mL) and diethyl ether (2×100 mL)
6. 6
   Dryingdried over anhydrous Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated

Procedure

To a solution of hydrazine monohydrate (44.0 mL, 1.00 mol) in ethanol (75 mL) at 0° C. in an ice-water bath was added 1-(2-bromoethoxy)-2-methoxyethane (13.6 mL, 0.100 mol) drop-wise over 20 minutes. The reaction was then allowed to warm to room temperature and stir for 5 minutes and then heated to 40° C. in a preheated oil bath for 12 hours. The reaction was then cooled to room temperature and concentrated to remove the ethanol. The remaining aqueous layer was extracted with methylene chloride (2×100 mL) and diethyl ether (2×100 mL). The organic layers were combined and dried over anhydrous Na2SO4, filtered and concentrated to provide [2-(2-methoxyethoxy)-ethyl]-hydrazine as a light yellow oil (10.29 g, 85%).

Source