Reaction #1519088

Reaction equation

tetraethylene glycol

NaOH

benzyl chloride

→

compound 23

Yield 71.0%

Tetraethylene glycol monobenzylether

Yield 71.0%

Solvents

NaCl

Conditions

Workup

1. 1
   workup.STIRRINGstirred overnight
2. 2
   TemperatureThe reaction mixture was cooled to room temperature
3. 3
   Washwashed CH2Cl2 (2×200 mL)
4. 4
   Washwashed sat. NaCl, dried MgSO4
5. 5
   Otherchromatographed (silica, ethyl acetate)

Procedure

To the oil of monodispersed tetraethylene glycol (19.4 g, 0.10 mol) was added a solution of NaOH (4.0 g in 4.0 mL) and the reaction was stirred for 15 mm. Then benzyl chloride (3.54 mL, 30.8 mmol) was added and the reaction mixture was heated to 100° C. and stirred overnight. The reaction mixture was cooled to room temperature, diluted with sat. NaCl (250 mL), and washed CH2Cl2 (2×200 mL). The organic layers were combined, washed sat. NaCl, dried MgSO4, and chromatographed (silica, ethyl acetate) to afford the monodispersed compound 23 as a yellow oil (6.21 g, 71% yield).

Source