2-Chloroethanol → HCID 58651784, compound

Temperature

80 °C

2-Mercaptoethyl ether (53.8 ml; 0.434 mol) was added to a solution of sodium hydroxide (17.36 g; 0.434 mol) in ethanol (300 ml) at ambient temperature and stirred for 15 min. 2-Chloroethanol (29.1 ml; 0.434 mol) was added to the solution at ambient temperature and after addition was complete the stirred solution was heated to 80° C. for 1 hr. The reaction mixture was then cooled to ambient temperature and the solid sodium chloride separated by filtration. The filtrate was transferred to a distillation apparatus and ethanol and unreacted 2-mercaptoethyl ether removed under vacuum (the latter distilling at 62° C. and 0.4 mbar). Fractional distillation of the remaining product yielded 2-[2-(2-mercapto-ethoxy)-ethylsulfanyl]-ethanol at 128° C. and 0.3 mbar. Pure fractions were combined to afford 2-[2-(2-mercapto-ethoxy)-ethylsulfanyl]-ethanol (31 g; 0.17 mol; 39% yield) as a colourless oil.

1. additionafter addition
2. temperatureThe reaction mixture was then cooled to ambient temperature
3. customthe solid sodium chloride separated by filtration
4. customremoved under vacuum (the latter
5. distillationdistilling at 62° C.
6. distillationFractional distillation of the remaining product

ORD record

ord-e2f78ff55c334bd7a1bca5e37c69a36c

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07335306B2