Vanillin → HCID 54028713, compound

HRID 982133Notes

Reaction equation

HRID 982133 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[OH-:12].[Na+].Br[CH2:15][CH:16]=[CH:17][CH2:18]Br>O>[CH2:15]([O:12][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7])[CH:16]=[CH:17][CH2:18][O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7]

Participants

5

Reactant 3

HCID 1183VanillinHCID 131802-Butene, 1,4-dibromo-HCID 14798Sodium Hydroxide

Product 1

HCID 54028713HCID 54028713, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of vanillin (30.4 g, 0.30 mol) dissolved in water (150 mL) containing sodium hydroxide (8.5 g) is added 1,4-dibromo-2-butene (21.4 g, 0.10 mol) and the reaction mixture is stirred and heated at reflux for 6 hours and then allowed to cool. The product is collected by filtration, washed with water and dried in air and then recrystallized from 200 mL of toluene and again collected by filtration and dried in air. The yield of 4,4'-[(2-butene-1,4-diyl)bis(oxy)bis(3-methoxybenzaldehyde)] obtained is 18.8 g (52.8% of theory). The identity of the product is supported by mass spectroscopy analysis.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. temperatureto cool
  4. filtrationThe product is collected by filtration
  5. washwashed with water
  6. customdried in air
  7. customrecrystallized from 200 mL of toluene
  8. filtrationagain collected by filtration
  9. customdried in air

Sources & evidence

ORD record
ord-f5e704881aa442a58f5cacd7cc611e93
Source dataset
uspto-grants-1991_02
Patent number
US04994512

Reaction notes

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