Ethylene Glycol → 2-Hydroxyethyl 2-Bromopropionate

Dicyclohexylcarbodimide (4.1 g, 20 mmol), anhydrous ethylene glycol (5.0 g, 81 mmol), and pyridine (1 ml, 12 mmol) were charged into a vial. Acetone (14 ml) and 2-bromopropionic acid (1.5 ml, 16.7 mmol) were added while cooling the vial down with an ice bath to control the exothermic reaction. After stirring the vial's contents overnight, undissolved by-products were removed by filtration. To the filtered reaction mixture were added AcOEt (20 ml) and saturated NaCl water (15 ml) followed by shaking well. The reaction mixture separated into 2 layers. The upper AcOEt layer was washed with dilute HCI once and saturated NaCl water (15 ml) two more times and then dried with MgSO4. After removing MgSO4, AcOEt was rotary evaporated to obtain a crude product. This crude product was purified by silica gel chromatography (eluent: AcOEt:hexane=1:1 by weight) to yield 1.4 g (43% yield) product.

1. temperaturewhile cooling the vial down with an ice bath
2. customthe exothermic reaction
3. customwere removed by filtration
4. customTo the filtered reaction mixture
5. stirringby shaking well
6. customThe reaction mixture separated into 2 layers
7. washThe upper AcOEt layer was washed with dilute HCI once
8. dry with materialsaturated NaCl water (15 ml) two more times and then dried with MgSO4
9. customAfter removing MgSO4, AcOEt
10. customwas rotary evaporated
11. customto obtain a crude product
12. customThis crude product was purified by silica gel chromatography (eluent: AcOEt:hexane=1:1 by weight)

ORD record

ord-ffd0459b5c534ef3b2862ee0adc95b82

Source dataset

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06342563B1