Ethanol → 2-[2-(2-formylphenoxy)ethoxy]benzaldehyde

HRID 1681563Notes

Reaction equation

HRID 1681563 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-:10].[Na+].Br[CH2:13][CH2:14]Br.[CH2:16]([OH:18])[CH3:17]>O>[CH:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][CH2:17][CH2:16][O:18][C:5]1[CH:3]=[CH:2][CH:8]=[CH:7][C:13]=1[CH:14]=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 6998SalicylaldehydeHCID 78391,2-DibromoethaneHCID 14798Sodium Hydroxide

Product 1

HCID 2242142-[2-(2-formylphenoxy)ethoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Salicylaldehyde (97.6 g) was dissolved in 80 cm3 of ethanol. An aqueous solution of sodium hydroxide (32 g) in 1 dm3 of water was added to give a yellow solution. 1,2-dibromoethane (73.6 g) was then added followed by sufficient ethanol to give an homogeneous solution. The mixture was stirred under nitrogen and heated to reflux temperature and maintained at reflux temperature under nitrogen for 44 hours. The mixture was allowed to cool and a solid precipitated. The solid was filtered off and dried. The solid was mixed with hexane at a temperature of about 65° C., sufficient chloroform was added to dissolve the solid and the mixture was allowed to cool and a solid crystallised. The solid had a melting point of 128°-130° C., corresponding closely to the reported melting point of 129° C. for 1,4-bis(2-formylphenyl)-1,4-dioxabutane.

Workup

  1. customto give a yellow solution
  2. customto give an homogeneous solution
  3. temperatureheated
  4. temperatureto reflux temperature
  5. temperaturemaintained
  6. temperatureat reflux temperature under nitrogen for 44 hours
  7. temperatureto cool
  8. customa solid precipitated
  9. filtrationThe solid was filtered off
  10. customdried
  11. additionThe solid was mixed with hexane at a temperature of about 65° C., sufficient chloroform
  12. additionwas added
  13. dissolutionto dissolve the solid
  14. temperatureto cool
  15. customa solid crystallised

Sources & evidence

ORD record
ord-e364b917e03e4fb9b824fbd6ed6a7b11
Source dataset
uspto-grants-1992_12
Patent number
US05173210

Reaction notes

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