Isobutyraldehyde → Morpholine, 4-(2-methyl-1-propenyl)-

HRID 128353Notes

Reaction equation

HRID 128353 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].[NH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1>O>[CH3:3][C:2]([CH3:4])=[CH:1][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 6561IsobutyraldehydeHCID 8083Morpholine

Product 1

HCID 102255Morpholine, 4-(2-methyl-1-propenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Isobutyraldehyde (19.4 g; 0.27 mol) is added slowly with stirring to morpholine (21.75 g; 0.25 mol). The ensuing reaction is exothermic. On completion of the addition the reaction mixture is stirred and heated at reflux for 5 hours while water (4.1 ml) is being azeotroped out of it. The reaction mixture is then vacuum distilled. A fraction collected at 64°-67° C. and 13 mm Hg weighs 15.6 g and consists of 90% by weight of title product and 10% by weight of morpholine. A second fraction collected at 67°-67.5° C. and 13 mm Hg (lit. 56°-57° C.; 11 mm Hg) weighs 16.2 g (46%) and is shown to be pure title product by nuclear magnetic resonance (nmr) and infrared (ir).

Workup

  1. customThe ensuing reaction
  2. additionOn completion of the addition the reaction mixture
  3. temperatureheated
  4. customis being azeotroped out of it
  5. distillationvacuum distilled
  6. customA fraction collected at 64°-67° C.
  7. customA second fraction collected at 67°-67.5° C.
  8. custom13 mm Hg (lit. 56°-57° C.; 11 mm Hg)

Sources & evidence

ORD record
ord-84e170bee893444291bb956204ec83da
Source dataset
uspto-grants-1981_03
Patent number
US04259486

Reaction notes

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