Ethyl Glycolate → Ethyl [(phenoxycarbonyl)oxy]acetate

HRID 2116593Notes

Reaction equation

HRID 2116593 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>[CH2:6]([O:5][C:1](=[O:4])[CH2:2][O:3][C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[CH3:7]

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-cf0d9d1fbee8447da77ee6e29fde22c4
Source dataset
uspto-grants-2008_10
Patent number
US07439257B2

Reaction notes

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