Ethyl Glycolate → Ethyl [(phenoxycarbonyl)oxy]acetate

HRID 912726Notes

Reaction equation

HRID 912726 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][OH:3].C(N(C(C)C)CC)(C)C.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>C1(C)C=CC=CC=1>[C:21]1([O:20][C:18]([O:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])=[O:19])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 12184Ethyl GlycolateHCID 15891Phenyl chloroformateHCID 81531Diisopropylethylamine

Product 1

HCID 12094709Ethyl [(phenoxycarbonyl)oxy]acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 25 g (240 mmol) of ethyl glycolate and of 55 ml (315 mmol) of diisopropylethylamine in 500 ml of toluene is admixed slowly at ambient temperature with 32 ml (256 mmol) of phenyl chloroformate. Stirring is continued at ambient temperature for 2 hours. The salt formed is separated off and the filtrate is concentrated under reduced pressure. This gives 53.7 g of oily product, used as it is in the following step.

Workup

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

Sources & evidence

ORD record
ord-91093377b6df4568b357e2d4bcbbc711
Source dataset
uspto-grants-2011_09
Patent number
US08026258B2

Reaction notes

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