4-Hydroxybenzaldehyde → HCID 54494362, compound

HRID 1533999Notes

Reaction equation

HRID 1533999 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:13][CH3:14])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.[OH-].[Na+].C(OCCOCCO)C>O>[CH:20]([C:19]1[CH:22]=[CH:23][C:16]([O:15][CH2:2][CH2:3][N:4]([CH2:13][CH3:14])[C:5]2[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=2)=[CH:17][CH:18]=1)=[O:21]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 8146Diethylene Glycol Monoethyl EtherHCID 14798Sodium HydroxideHCID 75842p-((2-Chloroethyl)ethylamino)benzaldehyde

Product 1

HCID 54494362HCID 54494362, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[[2-Chloroethyl]ethylamino]benzaldehyde 10.6 g (0.05 m), p-hydroxybenzaldehyde (6.1 g, 0.05 m), 50% NaOH (4.4 g), water (50 mL), and 2-(2-ethoxyethoxy)ethanol was heated at reflux for 6 hours and then allowed to cool. A semi-solid product was obtained which was washed with water by decantation and recrystallized from methanol. After being collected by filtration, washed with methanol, and dried in air the product weighed 6.5 g and the structure was confirmed by mass spectral analysis to be as follows: ##STR14##

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. temperatureto cool
  4. customA semi-solid product was obtained which
  5. washwas washed with water by decantation
  6. customrecrystallized from methanol
  7. filtrationAfter being collected by filtration
  8. washwashed with methanol
  9. customdried in air the product

Sources & evidence

ORD record
ord-bb816686fe284ed993b796f5fef28f99
Source dataset
uspto-grants-1992_02
Patent number
US05086161

Reaction notes

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