Ethanol → 4,4-Bis(hydroxymethyl)-1,3-oxazolidin-2-one

HRID 1025931Notes

Reaction equation

HRID 1025931 reaction equation
[NH2:1][C:2]([CH2:7][OH:8])([CH2:5][OH:6])[CH2:3][OH:4].[CH2:9]([OH:11])C>C(=O)(OCC)OCC>[OH:4][CH2:3][C:2]1([CH2:7][OH:8])[CH2:5][O:6][C:9](=[O:11])[NH:1]1

Participants

4

Reactant 2

HCID 702EthanolHCID 6503Tris(hydroxymethyl)aminomethane

Product 1

HCID 2455934,4-Bis(hydroxymethyl)-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 7766Diethyl CarbonateSolvent

Procedure

A suspension of 2-amino-2-(hydroxymethyl)propane-1,3-diol (51.37 g, 424.1 mmol) in diethyl carbonate (55 ml) was heated to 140° C. for 14 h, during which approximately 50 ml of ethanol was collected in a Dean-Stark trap. The reaction mixture was cooled to RT and the resulting thick, clear syrup was used without further purification. LRMS (ESI/APCI): 148 [M+H]+.

Workup

  1. customwas collected in a Dean-Stark trap
  2. customthe resulting thick, clear syrup was used without further purification

Sources & evidence

ORD record
ord-e3552fcf00ec4d56842b49d4ad0d8497
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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