4-Hydroxybenzaldehyde → 4-[6-(4-Formylphenoxy)hexoxy]benzaldehyde

HRID 73469Notes

Reaction equation

HRID 73469 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.[OH-:18].[K+].CN(C)[CH:22]=[O:23]>O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:18][C:2]2[CH:9]=[CH:8][C:5]([CH:22]=[O:23])=[CH:4][CH:3]=2)=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 123681,6-DibromohexaneHCID 14797Potassium Hydroxide

Product 1

HCID 108060504-[6-(4-Formylphenoxy)hexoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 73.3 g (0.6 mol) p-hydroxybenzaldehyde, 73.2 g (0.3 mol) 1,6-dibromohexane, 39.6 g (0.6 mol) potassium hydroxide and 240 ml dimethylformamide was heated under reflux, accompanied by stirring for 1 h, in a 500 ml three-necked flask with reflux condenser, internal thermometer and magnetic stirrer. After cooling the reaction mixture to room temperature, the obtained crystal slurry was placed in a 2-1 beaker containing 1 l of deionized water. The formed suspension was stirred intensively by means of a mechanical stirrer until the initially increased temperature had returned to room temperature. The crystals present were then filtered off, washed thoroughly with water and the product recrystallized from a mixture of 1200 ml ethanol and 300 ml water. After drying to constant weight in the vacuum drying cupboard at 70-80° C. 63.5 g (65% of the theoretical value) 1,6-bis(4-formylphenoxy)hexane (m.p.: 109.8-111.2° C.) was obtained in the form of white crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperaturewith reflux condenser
  4. stirringThe formed suspension was stirred intensively by means of a mechanical stirrer until the initially increased temperature
  5. customhad returned to room temperature
  6. filtrationThe crystals present were then filtered off
  7. washwashed thoroughly with water
  8. customthe product recrystallized from a mixture of 1200 ml ethanol and 300 ml water
  9. customAfter drying to constant weight in the vacuum
  10. customdrying cupboard at 70-80° C

Sources & evidence

ORD record
ord-b4ff055354a04820a90d661e9004a69b
Source dataset
uspto-grants-2014_09
Patent number
US08829067B2

Reaction notes

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