Phosgene → 2-Benzyloxyethyl chloroformate

HRID 328332Notes

Reaction equation

HRID 328332 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12](Cl)([Cl:14])=[O:13]>C1C=CC=CC=1>[Cl:14][C:12]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:13]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 121412-(Benzyloxy) ethanol

Product 1

HCID 45639002-Benzyloxyethyl chloroformate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

22.7 G. (150 mmoles) of 2-benzyloxyethanol is added dropwise with stirring to 188 ml. (300 mmoles) of a 17.2% phosgene solution in benzene cooled in an ice bath with protection from moisture. The addition is complete in 40 minutes and the solution is stirred in the ice bath for an additional hour. The reaction mixture is allowed to warm to room temperature and stirred overnight. A stream of nitrogen is passed through the solution to remove the excess phosgene and HCl. The reaction mixture is evaporated to dryness in vacuo affording 32.2 g. of a light orange residual oil. Infrared analysis reveals a strong carbonyl absorption and minimal hydroxy absorption. The material is used as is in the next step.

Workup

  1. additionThe addition
  2. stirringstirred overnight
  3. customto remove the excess phosgene and HCl
  4. customThe reaction mixture is evaporated to dryness in vacuo
  5. customaffording 32.2 g
  6. customa strong carbonyl absorption and minimal hydroxy absorption

Sources & evidence

ORD record
ord-8dc858325bea45d7af27b49092a4ff72
Source dataset
uspto-grants-1977_04
Patent number
US04017503

Reaction notes

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