Bicarbonate Ion → 4-Morpholinobenzaldehyde

HRID 1595366Notes

Reaction equation

HRID 1595366 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.[C:18](=O)([O-])[OH:19]>CN(C=O)C>[O:10]1[CH2:11][CH2:12][N:7]([C:1]2[CH:6]=[CH:5][C:4]([CH:18]=[O:19])=[CH:3][CH:2]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 24813Phosphorus oxychlorideHCID 623394-Phenylmorpholine

Product 1

HCID 2913494-Morpholinobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

N-Phenylmorpholine (77.2 g) was dissolved in DMF (150 ml) and phosphorus oxychloride (67.1 ml) was dropwise added in an ice bath. After the dropwise addition, the mixture was stirred at 60° C. for 22 hr. Ice water was added portionwise to the reaction mixture in an ice bath and the mixture was neutralized with a saturated aqueous hydrogencarbonate solution. The mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Isopropyl ether was added to the residue, and the precipitated crystals were collected by filtration to give the objective 4-morpholinobenzaldehyde (70.7 g), melting point 55° C.

Workup

  1. additionAfter the dropwise addition
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. additionIsopropyl ether was added to the residue
  6. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-07b9b77e00c34f2d886906baab46fceb
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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