Chlorosuccinimide → 2-Chloro-1,1,1-triethoxyethane

HRID 1253345Notes

Reaction equation

HRID 1253345 reaction equation
[CH2:1]([O:3][C:4]([O:9][CH2:10][CH3:11])([O:6][CH2:7][CH3:8])[CH3:5])[CH3:2].[Cl:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:12][CH2:5][C:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])[O:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 66221Triethyl orthoacetate

Product 1

HCID 3059222-Chloro-1,1,1-triethoxyethaneYield 77.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
40 °C

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).

Workup

  1. customirradiated with an ultraviolet lamp
  2. customsubsided upon completion of the reaction
  3. filtrationThe precipitated succinimide byproduct was filtered off
  4. concentrationthe filtrate was concentrated
  5. customto remove carbon tetrachloride
  6. distillationThe residual liquid was distilled

Sources & evidence

ORD record
ord-fe0932a5977c42c6afd2a5d028b3f7bc
Source dataset
uspto-grants-1988_05
Patent number
US04748280

Reaction notes

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