Ethylene Glycol → 2-(2-Bromopropyl)-1,3-dioxolane

Temperature

0 °C

Crotonaldehyde (9.18 g, 108 mmol) was added dropwise to a stirring solution of bromotrimethylsilane (24 g, 156 mmol) at 0° C., stirred for 1 hour at 0° C. then warmed to room temperature and stirred for a further 1 hour. Ethylene glycol (9.5 g, 156 mmol) and p-tolunesulphonic acid (100 mg) was added and the solution was heated to reflux, water was removed by use of Dean and Stark apparatus. On completion the mixture was cooled to room temperature and washed with aqueous sodiumhydrogen carbonate solution (saturated, 2×50 ml).The residue was purified by vacuum distillation to give 2-(2-bromopropyl)-1,3-dioxolane (18.8 g, 40–42° C. @1 mm Hg, 89%)

1. temperaturethen warmed to room temperature
2. stirringstirred for a further 1 hour
3. temperaturethe solution was heated
4. temperatureto reflux
5. customwater was removed by use of Dean and Stark apparatus
6. temperatureOn completion the mixture was cooled to room temperature
7. washwashed with aqueous sodiumhydrogen carbonate solution (saturated, 2×50 ml).The residue
8. distillationwas purified by vacuum distillation

ORD record

ord-cb81209c7d894b78b2580a1742d7efc6

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07122551B2