Vanillin → HCID 54028713, compound
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Vanillin (30.4 g, 0.20 m) is dissolved in water (150 mL), containing sodium hydroxide (8.5 g). 1,4-Dibromo-2-butene (21.4 g, 0.1 m) is added and the reaction mixture heated at reflux for 6 hours. After the reaction mixture is cooled, the product is collected by filtration, washed with water, dried in air, and finally recrystallized from toluene (200 mL). The yield is 18.8 g (52.8% of the theoretical yield) of 4,4'-[2-butene-1,4-diylbis(oxy)]bis[3-methoxybenzaldehyde] as indicated by mass spectroscopy analysis. A mixture of 4,4'-[2-butene-1,4-diylbis(oxy)]bis[3-methoxybenzaldehyde] (3.56 g, 0.01 m), ethyl cyanoacetate (2.26 g, 0.02 m), ethanol (90 mL), and piperidine (10 drops) is heated at reflux for 4 hours. The reaction mixture is cooled and the product is collected by filtration, washed with ethanol, and dried in air (yield--4.3 g). Mass spectrum analysis supports the following structure: ##STR30## In methylene chloride, the product has an absorption maximum at 316 nm.
Workup
- temperaturethe reaction mixture heated
- temperatureat reflux for 6 hours
- temperatureAfter the reaction mixture is cooled
- filtrationthe product is collected by filtration
- washwashed with water
- customdried in air
- customfinally recrystallized from toluene (200 mL)
Sources & evidence
- ORD record
- ord-50c38020738040ba8d83be768214569b
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04749774
Reaction notes
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