Water → 2-(2-Ethyl-2-methyl-1,3-oxazolidin-3-yl)ethan-1-ol

HRID 354714Notes

Reaction equation

HRID 354714 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[CH2:8]1[CH2:13]CC[CH2:10][CH2:9]1.O>C(C(C)=O)C>[CH2:8]([C:9]1([CH3:10])[N:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][O:4]1)[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 8078CyclohexaneHCID 8113Diethanolamine

Product 1

HCID 864992-(2-Ethyl-2-methyl-1,3-oxazolidin-3-yl)ethan-1-olYield 78%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A mixture of 315 g (3 mols) of diethanolamine, 432 g (6 mols) of methylethylketone, and 100 ml of cyclohexane is stirred and heated to reflux using a Dean-Stark trap to separate the water formed. The mixture is stirred and refluxed for a total of 311/2 hours during which 54 ml of aqueous layer, 85% water and 15% methyl ethyl ketone by NMR, is collected (85% of the theoretical amount of water of reaction). The mixture is then concentrated and the residue distilled to give 373 g (78% yield) of product (MEHEOX), b.p. 85°-88° C./2.5-3.0 mm Hg.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customto separate the water
  4. customformed
  5. stirringThe mixture is stirred
  6. customis collected (
  7. custom85% of the theoretical amount of water of reaction)
  8. concentrationThe mixture is then concentrated
  9. distillationthe residue distilled

Sources & evidence

ORD record
ord-5aa8e79cf06e4260bf6590ee5412c1af
Source dataset
uspto-grants-1983_03
Patent number
US04376844

Reaction notes

Loading…