Triethylamine → Ethyl [(phenoxycarbonyl)oxy]acetate

HRID 504064

Reaction equation

HRID 504064 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:12][OH:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:4]([C:2]([O:13][CH2:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])=[O:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12184Ethyl GlycolateHCID 15891Phenyl chloroformate

Product 1

HCID 12094709Ethyl [(phenoxycarbonyl)oxy]acetateYield 92.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

13.5 ml (105.6 mmol) of phenyl chloroformate are added, dropwise, at ambient temperature to a solution of 10 g (96.15 mmol) of ethyl glycolate and 27 ml (192.3 mmol) of triethylamine in 20 ml of toluene and the mixture is stirred at ambient temperature for 2 h. The salt formed is separated and the filtrate is concentrated under reduced pressure to obtain 20 g of oily product, which are used without modification in the following step.

Workup

  1. customThe salt formed
  2. customis separated
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-bbd48102c7484f56a47adf9e6ebbdf53
Source dataset
uspto-grants-2010_08
Patent number
US07777057B2

Linked notes

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