Toluene → 2-(3-Morpholin-4-YL-propoxy)-benzaldehyde

HRID 1112440Notes

Reaction equation

HRID 1112440 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[H-].[Na+].C1(C)C=CC=CC=1.Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C)C=O.O>[N:23]1([CH2:22][CH2:21][CH2:20][O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[CH:1]=[O:9])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6998SalicylaldehydeHCID 24758Sodium hydrideHCID 958344-(3-Chloropropyl)morpholine

Product 1

HCID 137952602-(3-Morpholin-4-YL-propoxy)-benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Salicylaldehyde (17g) is treated first with 6.7g of 50% sodium hydride in 110 ml of dimethylformamide and then with 92 ml of a 2N toluene solution of N-(3-chloropropyl)-morpholine. The mixture is heated at 105°-110° C for 4 hours, cooled and poured into 300 ml of water. The product is extracted three times with ether. The extracts are combined, dried, concentrated on a rotary evaporator and the residue distilled to give 32.3g of product as an oil, boiling point 155°-160° C at 0.1-0.2 mm of Hg.

Workup

  1. temperatureThe mixture is heated at 105°-110° C for 4 hours
  2. temperaturecooled
  3. extractionThe product is extracted three times with ether
  4. customdried
  5. concentrationconcentrated on a rotary evaporator
  6. distillationthe residue distilled

Sources & evidence

ORD record
ord-3f00ba42b812447a9db3498a217f25ca
Source dataset
uspto-grants-1978_10
Patent number
US04122255

Reaction notes

Loading…