Water → 4-(Morpholin-4-yl)benzoic acid

HRID 1837156Notes

Reaction equation

HRID 1837156 reaction equation
[N:1]1([C:7]2[CH:14]=[CH:13][C:10]([C:11]#N)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O1CCOCC1.[OH-:21].[K+].[OH2:23]>>[N:1]1([C:7]2[CH:14]=[CH:13][C:10]([C:11]([OH:23])=[O:21])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 3948084-Morpholinobenzonitrile

Product 1

HCID 3452784-(Morpholin-4-yl)benzoic acidYield 99%

Procedure

A solution of 4-(4-morpholinyl)benzonitrile (930 mg, 5.00 mmol) in 1:1 dioxane:water (20 mL) was treated with potassium hydroxide (1.12 g. 20 mmol). The mixture was heated at reflux for 96 h, concentrated, and the residue was dissolved in water. Upon acidification (pH˜2-3), a white precipitate resulted which was collected by filtration yielding 1.21 g (99%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 96 h
  3. concentrationconcentrated
  4. dissolutionthe residue was dissolved in water
  5. customUpon acidification (pH˜2-3), a white precipitate resulted which
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-87a7bacc4dae4ab5b2836b5d9eb97cc5
Source dataset
uspto-grants-2004_08
Patent number
US06780878B2

Reaction notes

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