Reaction #1265351

Reaction equation

Bromoacetic acid tert-butyl ester

triethylene glycol monomethyl ether

toluene

KOH

→

CH3(OCH2CH2)3CH2OCH2CO2C(CH3)3

Yield 12.0%

Solvents

Water

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was warmed to ambient temperature
2. 2
   workup.STIRRINGstirred for 1 h
3. 3
   Otherthe organic layer was separated
4. 4
   WashThe organic layer was washed with saturated aq. NH4Cl (2×100 mL), saturated aq. NaHCO3 (100 mL), brine (100 mL)
5. 5
   Dryingdried over anhydrous MgSO4
6. 6
   ConcentrationThe solution was concentrated in vacuo
7. 7
   Washeluted with ethyl acetate

Procedure

Bromoacetic acid tert-butyl ester (20 mL, 0.14 mol), was added over a 10 min period to a rapidly stirred mixture of triethylene glycol monomethyl ether (20 mL, 0.13 mol), tetrabutyl ammonium bromide (20 g, 0.062 mol), toluene (100 mL) and KOH (50% w/w, 100 mL), and the resulting heterogeneous reaction mixture was stirred at 0° C. for 10 min. The reaction mixture was warmed to ambient temperature and stirred for 1 h. Water (100 mL) was added and the organic layer was separated. The organic layer was washed with saturated aq. NH4Cl (2×100 mL), saturated aq. NaHCO3 (100 mL), brine (100 mL), and dried over anhydrous MgSO4. The solution was concentrated in vacuo and the residue was loaded onto a silica gel gravity column (200 g) and eluted with ethyl acetate to afford CH3(OCH2CH2)3CH2OCH2CO2C(CH3)3 as a colorless oil (420 g, 12%).

Source