Toluene → 4-(2-Hydroxyethyl)morpholin-3-one
Reaction equation
[K].[C:2]1([CH3:8])C=CC=CC=1.[NH:9]([CH2:13][CH2:14][OH:15])[CH2:10][CH2:11][OH:12].ClCC(OC)=[O:19]>CO>[OH:12][CH2:11][CH2:10][N:9]1[CH2:8][CH2:2][O:15][CH2:14][C:13]1=[O:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Potassium tert-butoxyde (176 g, 1.1 eq.) was added to 1440 ml of toluene. The suspension was heated to 75° C. and maintained for 30 minutes until complete dissolution of the white solid. At this temperature diethanolamine (150 g, 1 eq.) was slowly added. The thick pale yellow suspension was maintained with strong stirring for 30 minutes and methyl chloroacetate (163 g, 1.05 eq.) was added slowly. The solution was maintained at the same temperature for two hours. To the warm mixture methanol (600 ml) was added and cooled at room temperature, salts were filtrated and the organic layer concentrated until dry. Compound (IV) was obtained as an orange oil (204 g, 98%) which was distilled under high vacuum to obtain it as a highly pure colorless oil (80%, bp5 180° C.). IR (film) (n cm-1): 3410, 2934, 2874, 1633, 1501, 1350, 1141. MS (EI), (m/z, %): 145 (M+, 12), 114 (M-CH2OH, 100), 86 (M-NC2H4OH, 65), 74 (M-71, 7), 56 (M-89, 41), 42 (M-103, 44).
Workup
- temperaturemaintained for 30 minutes until complete dissolution of the white solid
- temperatureThe thick pale yellow suspension was maintained
- temperatureThe solution was maintained at the same temperature for two hours
- temperaturecooled at room temperature
- filtrationsalts were filtrated
- concentrationthe organic layer concentrated
- customuntil dry
Sources & evidence
- ORD record
- ord-06bf9ad4fe444aada5cc73d2a92b5f3f
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143463B2
Reaction notes
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