Dimethylformamide → 2-Hydroxy-4-morpholin-4-yl-benzaldehyde

HRID 884422Notes

Reaction equation

HRID 884422 reaction equation
CN([CH:4]=[O:5])C.P(Cl)(Cl)(Cl)=O.[N:11]1([C:17]2[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C([O-])(=O)C.[Na+]>O>[OH:23][C:19]1[CH:18]=[C:17]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH:22]=[CH:21][C:20]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 1413433-MorpholinophenolHCID 517045Sodium Acetate

Product 1

HCID 98156592-Hydroxy-4-morpholin-4-yl-benzaldehydeYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DMF (10 mL) was treated dropwise with phosphorus oxychloride (2.3 g, 15 mmol). The reaction was kept at 25° C. by cooling on ice. The reaction mixture was treated with 3-(4-morpholinyl)phenol (2.5 g, 14 mmol) in small portions, stirred for 30 min at room temperature, then stirred at 100° C. for 8 h. After cooling, the mixture was poured into aqueous sodium acetate (1 M, 40 mL) and 10 mL of water was added. The resulting precipitate was collected by filtration, washed with water (10 mL), air dried, and purified by flash chromatography (silica gel, 4×7.5 cm, eluted with 90/10 CHCl3/ether) to yield the product as a light gray solid (0.66 g, 23%). See U.S. Pat. No. 4,147,552.

Workup

  1. customwas kept at 25° C.
  2. temperatureby cooling on ice
  3. stirringstirred at 100° C. for 8 h
  4. temperatureAfter cooling
  5. additionwas added
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water (10 mL), air
  8. customdried
  9. custompurified by flash chromatography (silica gel, 4×7.5 cm, eluted with 90/10 CHCl3/ether)

Sources & evidence

ORD record
ord-d0dd1d50852849818a1993c0c952f1b1
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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