Vanillin → 4-(Benzyloxy)-3-methoxybenzaldehyde

HRID 1586629Notes

Reaction equation

HRID 1586629 reaction equation
[OH-].[Na+].[O:3]=[CH:4][C:5]1[CH:13]=[CH:12][C:10]([OH:11])=[C:7]([O:8][CH3:9])[CH:6]=1.Cl[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH2:15]([O:11][C:10]1[CH:12]=[CH:13][C:5]([CH:4]=[O:3])=[CH:6][C:7]=1[O:8][CH3:9])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 1183VanillinHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 755064-(Benzyloxy)-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (2.4 g) is dissolved in water (50 mL) by stirring. Vanillin (7.60 g, 0.05 mol) and α-chloro-toluene (7.60 g, 0.06 mol) are added and the reaction mixture is heated at reflux with stirring for 16 hours. The product is extracted from the aqueous mixture using methylene chloride (10 mL). When the solvent is removed under vacuum an oil results which crystallizes when treated with isopropyl alcohol and stirred. Mass spectrometry supports the following structure: ##STR17##

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux
  3. stirringwith stirring for 16 hours
  4. extractionThe product is extracted from the aqueous mixture
  5. customWhen the solvent is removed under vacuum an oil
  6. customresults which
  7. customcrystallizes when
  8. additiontreated with isopropyl alcohol
  9. stirringstirred

Sources & evidence

ORD record
ord-ccfb9adc7f1949e29b60a6ff55192654
Source dataset
uspto-grants-1993_06
Patent number
US05215876

Reaction notes

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