Vanillin → 4-[3-(4-Formyl-2-methoxyphenoxy)-2-hydroxypropoxy]-3-methoxybenzaldehyde

HRID 579820Notes

Reaction equation

HRID 579820 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+].Cl[CH2:15][CH:16]([OH:19])[CH2:17]Cl>O>[OH:19][CH:16]([CH2:17][O:12][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7])[CH2:15][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 72891,3-Dichloro-2-propanolHCID 14798Sodium Hydroxide

Product 1

HCID 12341104-[3-(4-Formyl-2-methoxyphenoxy)-2-hydroxypropoxy]-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Vanillin (91.2 g, 0.60 mol) is dissolved in water (500 mL) containing sodium hydroxide (24.0 g). To this solution is added 1,3-dichloro-2-propanol (38.7 g, 0.30 mol) and the reaction mixture is stirred and heated at reflux for 8 hours. Upon cooling to room temperature the product crystallizes and is collected by filtration, washed with water and dried. The crude product is recrystallized from 2 L ethanol, filtered, washed with ethanol and air dried. The purified product, 4,4'-[(2-hydroxy-1,3-propanediyl)bis(oxy)]bis[3-methoxybenzaldehyde], is obtained as a white solid in a yield of 74.3 g; 68.7% of theory. Mass spectroscopy analysis supports the structure: ##STR23## A mixture of 4,4'-[(2-hydroxy-1,3-propanediyl)bis[3-methoxy-benzaldehyde] (3.60 g, 0.01 m), ethyl cyanoacetate (2.26 g, 0.02 m), ethanol (100 mL), piperidine (10 drops), and acetic acid (5 drops) is heated at reflux for 4 hours and then allowed to cool. The essentially white product is collected by filtration, washed with ethanol, and dried in air (yield--3.5 g). Mass spectrum analysis supports the following structure: ##STR24## The product, diethyl 3,3'-[(2-hydroxy-1,3-propanediyl)bis(oxy)bis(3-methoxy-4,1-phenylene)]bis[2-cyano-2-propenoate], has an absorption maximum (λmax) at 360 nm in methylene chloride.

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 hours
  3. customcrystallizes
  4. filtrationis collected by filtration
  5. washwashed with water
  6. customdried
  7. customThe crude product is recrystallized from 2 L ethanol
  8. filtrationfiltered
  9. washwashed with ethanol and air
  10. customdried

Sources & evidence

ORD record
ord-610a83a1b97b4f4a9a6f9b88d941533c
Source dataset
uspto-grants-1988_06
Patent number
US04749774

Reaction notes

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