Phosgene → 2(2-n-Butoxyethoxy)-ethyl chloroformate

HRID 328330

Reaction equation

HRID 328330 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11])[CH2:2][CH2:3][CH3:4].[C:12](Cl)([Cl:14])=[O:13]>C1C=CC=CC=1>[Cl:14][C:12]([O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:13]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 8177Diethylene Glycol Monobutyl Ether

Product 1

HCID 138287912(2-n-Butoxyethoxy)-ethyl chloroformate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

24.3 G. (150 mmoles) of 2-(2-n-butoxyethoxy)ethanol is added dropwise with stirring to 250 ml. (290 mmoles) of a 12.5% phosgene solution in benzene, cooled in an ice bath and protected from moisture. The addition is carried out over a period of approximately 1 1/2 hours and stirring is continued in an ice bath for 2 hours. The solution is allowed to warm to room temperature and stirred overnight. Nitrogen is passed through the solution for several hours to remove excess phosgene and excess HCl. The solvent is removed in vacuo affording 32.9 g. of a colorless oil. The infrared spectrum revealed a strong carbonyl absorption and no hydroxy absorption. The oil is used without any further purification in the next step.

Workup

  1. additionThe addition
  2. stirringstirring
  3. waitis continued in an ice bath for 2 hours
  4. stirringstirred overnight
  5. waitNitrogen is passed through the solution for several hours
  6. customto remove excess phosgene and excess HCl
  7. customThe solvent is removed in vacuo
  8. customaffording 32.9 g
  9. customa strong carbonyl absorption
  10. customno hydroxy absorption
  11. customThe oil is used without any further purification in the next step

Sources & evidence

ORD record
ord-73c9eba9fb10439d8754a85b3b7f4ff9
Source dataset
uspto-grants-1977_04
Patent number
US04017503

Linked notes

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