Toluene → HCID 131726611, compound

Temperature

0 °C

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 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%).

1. temperatureThe reaction mixture was warmed to ambient temperature
2. stirringstirred for 1 h
3. customthe organic layer was separated
4. washThe organic layer washed with saturated aq. NH4Cl (2×100 mL), saturated aq. NaHCO3 (100 mL), brine (100 mL)
5. dry with materialdried over anhydrous MgSO4
6. concentrationThe solution was concentrated in vacuo
7. washeluted with ethyl acetate

ORD record

ord-41205521d5bb4e0688cb61b94556704f

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07494714B2