4-Hydroxybenzaldehyde → 4-(2-Morpholinoethoxy)benzaldehyde

HRID 1768546Notes

Reaction equation

HRID 1768546 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholine

Product 1

HCID 37199024-(2-Morpholinoethoxy)benzaldehydeYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

92.8 g of 4-hydroxybenzaldehyde are dissolved in 820 ml of dimethylformamide. After the addition of 228 g of 4-(2-chloroethyl)morpholine and 415 g of finely powdered potassium carbonate the reaction mixture is heated to 100° overnight under argon and while stirring vigorously. The cooled solution is poured into 3 l of ice-water, extracted with ethyl acetate, washed with water, dried and evaporated. The residual dark oil is distilled in a high vacuum and gives 132 g of 4-(2-morpholinoethoxy)benzaldehyde as a yellowish oil, boiling point 145°-150°/33 Pa.

Workup

  1. temperatureis heated to 100° overnight under argon
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. distillationThe residual dark oil is distilled in a high vacuum

Sources & evidence

ORD record
ord-bf01c8d0b43c433a87d19b5b8bbd66e1
Source dataset
uspto-grants-1995_01
Patent number
US05378705

Reaction notes

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