Reaction #4016

Reaction equation

1,1,1-triethoxyethane

N-chlorosuccinimide

→

2-chloro-1,1,1-triethoxyethane

Yield 77.1%

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Otherirradiated with an ultraviolet lamp
2. 2
   Othersubsided upon completion of the reaction
3. 3
   FiltrationThe precipitated succinimide byproduct was filtered off
4. 4
   Concentrationthe filtrate was concentrated
5. 5
   Otherto remove carbon tetrachloride
6. 6
   workup.DISTILLATIONThe residual liquid was distilled

Procedure

A mixture of 1,1,1-triethoxyethane (97.3 g) and N-chlorosuccinimide (88.1 g) in carbon tetrachloride (600 ml) was warmed to 40° C. and then irradiated with an ultraviolet lamp. The reaction became exothermic and then subsided upon completion of the reaction. The precipitated succinimide byproduct was filtered off and the filtrate was concentrated to remove carbon tetrachloride. The residual liquid was distilled to obtain pure 2-chloro-1,1,1-triethoxyethane (91.0 g; b.p. 91° C./25 mm).

Source