Toluene → 2-(2-Morpholinoethoxy)benzaldehyde

HRID 26965

Reaction equation

HRID 26965 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][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>CN(C)C=O.O>[N:22]1([CH2:21][CH2:20][O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[CH:1]=[O:9])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6998SalicylaldehydeHCID 24758Sodium hydrideHCID 767274-(2-Chloroethyl)morpholine

Product 1

HCID 9765932-(2-Morpholinoethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Salicylaldehyde (34 g) is treated first with 13.4 g of 50% sodium hydride in 220 ml of dimethylformamide and then with 185 ml of a 2 N toluene solution of N-(2-chloroethyl)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 56.6 g of product as an oil, boiling point 145°-150° C. at 0.05-0.1 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-fbafb2d7eed545b084420b6dd93457c8
Source dataset
uspto-grants-1979_04
Patent number
US04151354

Linked notes

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