Reaction equation
[CH2:1]([CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)[CH3:2].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[OH2:16].[C:17]1([CH3:27])C=CC(S(O)(=O)=O)=CC=1.[OH2:28].[C:29]1([CH3:35])C=CC=CC=1>>[CH2:29]([O:16][C:2](=[O:28])[CH:1]=[C:3]1[CH2:8][CH:7]([CH2:17][CH3:27])[CH2:6][CH:5]=[C:4]1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH3:35]Participants
6
Conditions
- Temperature
- 100 °C
Procedure
91.6 g of 4-Ethyl-cyclohexanone, 73.6 g of morpholine and 2 g of p-toluene-sulfonic acid monohydrate are dissolved in 400 ml of toluene. The mixture is heated to reflux and the water formed is removed by a water separator. After reacting for about 24 h, the reaction mixture is cooled to 100° C. and 2 g of p-toluene-sulfonic acid are added, followed by the addition of 157.22 g of glyoxylic acid ethyl ester during 30 minutes. The mixture is again heated to reflux for 5 hours and allowed to cool down to 22° C. The solvent is evaporated in vacuo and the crude product is distilled in vacuo at 140-150° C./9.5−2 mbar.
Workup
- temperatureThe mixture is heated
- temperatureto reflux
- customis removed by a water separator
- addition2 g of p-toluene-sulfonic acid are added
- additionfollowed by the addition of 157.22 g of glyoxylic acid ethyl ester during 30 minutes
- temperatureThe mixture is again heated
- temperatureto reflux for 5 hours
- temperatureto cool down to 22° C
- customThe solvent is evaporated in vacuo
- distillationthe crude product is distilled in vacuo at 140-150° C./9.5−2 mbar
Sources & evidence
- ORD record
- ord-56376add803b45279b12c1ab4a728805
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906677B2
Linked notes
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