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

HRID 49831

Reaction equation

HRID 49831 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-7ad0d7d1880144fa87a13458aa991f81
Source dataset
uspto-grants-2004_03
Patent number
US06710057B2

Linked notes

Loading…