Benzyl Chloride → 4-Benzyloxy-3-ethoxybenzaldehyde

HRID 1881183Notes

Reaction equation

HRID 1881183 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2].[OH-].[Na+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([O:12][C:11]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[O:3][CH2:1][CH3:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8467EthylvanillinHCID 14798Sodium Hydroxide

Product 1

HCID 5613644-Benzyloxy-3-ethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of 3-ethoxy-4-hydroxy-benzaldehyde (83 g) in N,N-dimethylformamide (400 ml) was gradually added 10 M sodium hydroxide (55 ml) and then benzyl chloride (60 ml) was added at a temperature under 40° C. The mixture was stirred at room temperature for a half an hour and for 2 hours at 60° C. The solution was poured into ice-cold water (2 l) and extracted with diethyl ether. The organic phase was washed with water and 5M sodium hydroxide and then it was dried and evaporated. The product was recrystallized from toluene-heptane.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed with water and 5M sodium hydroxide
  3. customit was dried
  4. customevaporated
  5. customThe product was recrystallized from toluene-heptane

Sources & evidence

ORD record
ord-0a527ceb74154c2685d70c2ba333f087
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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