Ethylene Oxide → 218594-92-4

HRID 1923453Notes

Reaction equation

HRID 1923453 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:7][O:6][CH2:5][CH2:4][NH:3]1.[CH3:9][C:10](C)=[O:11].C(=O)=O.C1OC1>CO>[CH3:1][C:2]1([CH3:8])[CH2:7][O:6][CH2:5][CH2:4][N:3]1[CH2:9][CH2:10][OH:11]

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 145518493,3-DimethylmorpholineHCID 18522661Acetone cardice

Product 1

HCID 22342910218594-92-4Yield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a pressure vessel containing 3,3-dimethylmorpholine (12.15 g, 106 mmol) in MeOH (17 mL) at −78° C. (external temperature, acetone/CO2(s)) was added ethylene oxide (6.2 mL, 125 mmol, 1.2 equiv., condensed at −78° C.). The solution was sealed and stirred over 20 hours, during which time the temperature warmed to room temperature. The reaction mixture was concentrated in vacuo and the crude product was distilled (75° C., 0.5 torr) to provide 2-(3,3-dimethyl-morpholin-4-yl)-ethanol (14 g, 82%) as a colorless oil contaminated with ˜15% of 3,3-dimethyl-morpholine. LC/MS found 160.10 (M++H, C8H18NO2 requires 160.13).

Workup

  1. customThe solution was sealed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. distillationthe crude product was distilled (75° C., 0.5 torr)

Sources & evidence

ORD record
ord-8680a40a168b40a7b89a988e8552925d
Source dataset
uspto-grants-2012_05
Patent number
US08178491B2

Reaction notes

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