1-Morpholinoethanol → HCID 13335983, compound

HRID 979984Notes

Reaction equation

HRID 979984 reaction equation
[Cl:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[C:4]([C:13](=[O:16])[CH2:14][CH3:15])[CH:3]=1.[Na].[O:18]1[CH2:23][CH2:22][N:21]([CH:24](O)C)[CH2:20][CH2:19]1>>[Cl:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH2:10][CH2:24][N:21]2[CH2:22][CH2:23][O:18][CH2:19][CH2:20]2)=[O:8])[C:5]([OH:12])=[C:4]([C:13](=[O:16])[CH2:14][CH3:15])[CH:3]=1

Participants

4

Reactant 3

HCID 30293761-MorpholinoethanolHCID 5360545SodiumHCID 13335980HCID 13335980, compound

Product 1

HCID 13335983HCID 13335983, compoundYield 88.8%

Procedure

A 24.3 g (0.10 mole) quantity of methyl 5-chloro-3-propionylsalicylate was added to a solution of 0.5 g (0.022 mole) of sodium in 300 ml of morpholinoethanol. The mixture was maintained at room temperature for 24 hours and was heated at 2 hours at 90° C. The reaction mixture was subjected to distillation at reduced pressure to remove the excess unreacted morpholinoethanol and the methanol produced, and the residue was recrystallized from cyclohexane to obtain 38.0 g (88.8%) of crystals which melt at 144.0° to 146.3° C.

Workup

  1. temperaturewas heated at 2 hours at 90° C
  2. distillationThe reaction mixture was subjected to distillation at reduced pressure
  3. customto remove the excess unreacted morpholinoethanol
  4. customthe methanol produced
  5. customthe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-f478ea3b97504371bf9d97b2daa64432
Source dataset
uspto-grants-1987_01
Patent number
US04634768

Reaction notes

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