Allyl chloride → Ethyl [(prop-2-en-1-yl)oxy]carbamate

HRID 903004

Reaction equation

HRID 903004 reaction equation
[OH:1][NH:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:8](Cl)[CH:9]=[CH2:10].[OH-].[K+]>C(O)C>[CH2:10]([O:1][NH:2][C:3](=[O:4])[O:5][CH2:6][CH3:7])[CH:9]=[CH2:8]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 11510HydroxyurethaneHCID 14797Potassium Hydroxide

Product 1

HCID 19860187Ethyl [(prop-2-en-1-yl)oxy]carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

100 g of N-hydroxyurethane and 80.3 g of allyl chloride were added, at 20° C., to a solution of 53.8 g of potassium hydroxide in 750 ml of ethanol. The mixture was stirred and refluxed (80° C.) for 4 hours, then was cooled to 25° C. and filtered. The solvent was evaporated from the filtrate and the residue, an oil, was distilled, 51°-55° C., 0.2 Torr., to give ethyl (2-propenyloxy)carbamate, 3A, as a colorless oil.

Workup

  1. temperaturewas cooled to 25° C.
  2. filtrationfiltered
  3. customThe solvent was evaporated from the filtrate
  4. distillationthe residue, an oil, was distilled, 51°-55° C.

Sources & evidence

ORD record
ord-0eda31aec55b414b8acdd83dfd38cd52
Source dataset
uspto-grants-1980_10
Patent number
US04226612

Linked notes

Loading…