Phosgene → Ethyl 4-(chlorocarbonyloxy)-2-butynoate

HRID 649368Notes

Reaction equation

HRID 649368 reaction equation
[C:1](Cl)([Cl:3])=[O:2].[OH:5][CH2:6][C:7]#[C:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>C1C=CC=CC=1>[Cl:3][C:1]([O:5][CH2:6][C:7]#[C:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:2]

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 108554684-Hydroxy-but-2-ynoic acid ethyl ester

Product 1

HCID 14567687Ethyl 4-(chlorocarbonyloxy)-2-butynoateYield 85%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 40 ml of a benzene solution of phosgene (containing 6.2 g (62.5 millimoles) of phosgene), 6.4 g (50 millimoles) of ethyl 4-hydroxy-2-butynoate was rapidly added under cooling with ice, and the mixture was stirred for 30 minutes under cooling with ice. The reaction mixture was returned to room temperature and left to stand for one night. Then, the reaction mixture was concentrated under reduced pressure to distil off benzene, whereby 8.1 g (yield: 85%) of oily ethyl 4-(chlorocarbonyloxy)-2-butynoate was obtained as the residue.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. customwas returned to room temperature
  4. waitleft
  5. waitto stand for one night
  6. concentrationThen, the reaction mixture was concentrated under reduced pressure
  7. customto distil off benzene

Sources & evidence

ORD record
ord-94fb078edcf84d3eae5bfec031bcddbf
Source dataset
uspto-grants-1988_04
Patent number
US04739106

Reaction notes

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