Salicylaldehyde → 2-(Benzyloxy)benzaldehyde

HRID 1632957Notes

Reaction equation

HRID 1632957 reaction equation
[OH-].[Na+].[CH:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O.CC(C)=O>[CH2:12]([O:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[CH:3]=[O:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6998SalicylaldehydeHCID 7498Benzyl BromideHCID 14798Sodium Hydroxide

Product 1

HCID 3447842-(Benzyloxy)benzaldehydeYield 132.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

Sodium hydroxide (20.0 gms.; 0.5 mole) was dissolved in 150 ml H2O and salicylaldehyde (53.2 ml; 0.5 mole) dissolved in 200 ml acetone was added, followed by benzyl bromide (65.4 ml; 0.55 mole) dissolved in 200 ml acetone. The reaction mixture was refluxed for a period of 24 hours and allowed to cool. The acetone was evaporated in vacuum and the two phase residue extracted with 300 ml CH2Cl2. The CH2Cl2 layer was washed with 150 ml H2O and dried over anhydrous Na2SO4. The Na2SO4 was filtered off and the solvent removed from the filtrate to yield 141 grams of the crude product.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for a period of 24 hours
  3. temperatureto cool
  4. customThe acetone was evaporated in vacuum
  5. extractionthe two phase residue extracted with 300 ml CH2Cl2
  6. washThe CH2Cl2 layer was washed with 150 ml H2O
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationThe Na2SO4 was filtered off
  9. customthe solvent removed from the filtrate

Sources & evidence

ORD record
ord-1c3accc3c9364f7cb5569500c5e7bec1
Source dataset
uspto-grants-1984_10
Patent number
US04478834

Reaction notes

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