Salicylaldehyde → 2-(Benzyloxy)benzaldehyde

HRID 1020277Notes

Reaction equation

HRID 1020277 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:10]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 3447842-(Benzyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Salicylaldehyde (50 mmoles) was dissolved in dry dimethylformamide (DMF) (100 ml) at room temperature. Benzyl bromide (75 mmoles) was then added followed by the potassium carbonate (125 mmoles) and the mixture stirred at room temperature for 48 h. The mixture is then filtered to remove the potassium carbonate and the filtrate is mixed with ethyl acetate. The organic phase is washed with water (3×200 ml), brine and dried over MgSO4. The solution is then filtered and evaporated in vacuo to provide the crude material. Solid products are washed with ethyl ether to provide the clean desired product or in the case of aldehydes which are oils, they are purified by silica gel chromatography.

Workup

  1. filtrationThe mixture is then filtered
  2. customto remove the potassium carbonate
  3. additionthe filtrate is mixed with ethyl acetate
  4. washThe organic phase is washed with water (3×200 ml), brine
  5. dry with materialdried over MgSO4
  6. filtrationThe solution is then filtered
  7. customevaporated in vacuo
  8. customto provide the crude material
  9. washSolid products are washed with ethyl ether

Sources & evidence

ORD record
ord-3cf262724f65426fb3b6813481f86f93
Source dataset
uspto-grants-2014_05
Patent number
US08716319B2

Reaction notes

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