Chloroethane → HCID 18945618, compound

HRID 399932Notes

Reaction equation

HRID 399932 reaction equation
[Na].[OH:2][N:3]1[C:7](=[O:8])[CH:6]2[CH2:9][CH2:10][CH:11]=[CH:12][CH:5]2[C:4]1=[O:13].[CH2:14](Cl)[CH3:15]>C(OC)(C)(C)C>[CH2:14]([O:2][N:3]1[C:4](=[O:13])[CH:5]2[CH2:12][CH2:11][CH:10]=[CH:9][CH:6]2[C:7]1=[O:8])[CH3:15]

Participants

5

Reactant 3

HCID 6337Chloroethane2×HCID 5360545SodiumHCID 21940951HCID 21940951, compound

Product 1

HCID 18945618HCID 18945618, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

In an autoclave 60 g of a 20 wt % solution of the sodium salt of N-hydroxytetrahydrophthalimide (0.063 mol), 20 ml of methyl tert-butyl ether and 5.0 g of ethyl chloride were mixed together. The mixture was heated to 100° C. After reaching this temperature the mixture was stirred for a further 5 hours while the temperature was maintained at 100° C. After 5 hours' reaction the excess ethyl chloride was blown out and the reaction mixture was discharged. The reaction mixture was composed of two liquid layers which were separated. The ether layer was analysed by gas chromatography. A yield of 81% of N-ethoxytetrahydrophthalimide (0.051 mol) was found.

Workup

  1. temperaturewas maintained at 100° C
  2. customwere separated

Sources & evidence

ORD record
ord-354853b177f847388c8855e26e1cb8fd
Source dataset
uspto-grants-1998_10
Patent number
US05824804

Reaction notes

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