Toluene → HCID 77315, compound

HRID 1262466Notes

Reaction equation

HRID 1262466 reaction equation
[C:1]1(=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[O:17]1[CH2:18][CH2:19][N:14]([C:1]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 8083MorpholineHCID 13246Cyclododecanone

Product 1

HCID 77315HCID 77315, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

A two liter three-necked flask was charged with 366 grams (2.0 moles) cyclododecanone, 348 grams (4.0 moles) morpholine, 600 ml toluene and 3.0 grams (0.0158 moles) para-toluene sulfonic acid catalyst. A magnetic stir bar was added along with a few carbon boiling chips. A Dean-Stark water trap and condenser were then attached and the mixture brought to reflux with stirring. After 46 hours reflux, 75 ml. of aqueous phase had been collected. The mixture was then cooled and the excess toluene and morpholine removed at reduced pressure (25-50 mm Hg). The residue was then distilled under vacuum (0.6 mm Hg) to yield 300.5 grams of a viscous clear oil, 1-morpholino-1-cyclododecene, b.p. 135°-150° C., 60% yield.

Workup

  1. additionA magnetic stir bar was added along with a few carbon boiling chips
  2. temperatureto reflux
  3. temperatureAfter 46 hours reflux
  4. customof aqueous phase had been collected
  5. temperatureThe mixture was then cooled
  6. customthe excess toluene and morpholine removed at reduced pressure (25-50 mm Hg)
  7. distillationThe residue was then distilled under vacuum (0.6 mm Hg)

Sources & evidence

ORD record
ord-13a85035f1c24f90842c580485402576
Source dataset
uspto-grants-1984_06
Patent number
US04452632

Reaction notes

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