Ethyl Glycolate → Ethyl [(phenoxycarbonyl)oxy]acetate

HRID 1640401Notes

Reaction equation

HRID 1640401 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(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[C:5]1([O:4][C:2]([O:13][CH2:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])=[O:3])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 12184Ethyl GlycolateHCID 15891Phenyl chloroformateHCID 81531Diisopropylethylamine

Product 1

HCID 12094709Ethyl [(phenoxycarbonyl)oxy]acetateYield 99.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

32 ml (256 mmol) of phenyl chloroformate are added slowly at room temperature to a solution of 25 g (240 mmol) of ethyl glycolate and 55 ml (315 mmol) of diisopropylethylamine in 500 ml of toluene. Stirring is continued at room temperature for 2 hours. The salt formed is separated out and the filtrate is concentrated under reduced pressure. 53.7 g of oily product are obtained, and are used without further purification in the following step.

Workup

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

Sources & evidence

ORD record
ord-518e9f9c6410471d976d610457e3ca2f
Source dataset
uspto-grants-2012_02
Patent number
US08114866B2

Reaction notes

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