Potassium Hydroxide → 4-(2-Hydroxyethyl)morpholin-3-one

HRID 385980Notes

Reaction equation

HRID 385980 reaction equation
ClCC([O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][C:9]1=[O:14])=O.[OH-].[K+]>CO>[OH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][C:9]1=[O:14]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 152873992-(3-Oxomorpholino)ethyl 2-chloroacetate

Product 1

HCID 152874004-(2-Hydroxyethyl)morpholin-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 2-(3-oxomorpholino)ethyl 2-chloroacetate (400 g, 1.81 mol) in methanol (2 L) was added dropwise to a cooled (15° C.) solution of potassium hydroxide (203 g, 3.62 mol) in methanol (10 L). This was followed by the addition methanol (3 L). The resulting solution was allowed to react overnight while the temperature was maintained at room temperature. The mixture was then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue taken up in 1 L of dichloromethane, washed with 250 ml of water, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification was performed by distillation under reduced pressure (0.08 mm Hg) collecting the fraction that came over at 140° C. to afford the title compound.

Workup

  1. customto react overnight while the temperature
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washwashed with 250 ml of water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification
  9. distillationwas performed by distillation under reduced pressure (0.08 mm Hg)
  10. customcollecting the fraction that
  11. customcame over at 140° C.

Sources & evidence

ORD record
ord-576769e0f10c4f5fa8b71931d5ffcce8
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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