Salicylaldehyde → Benzaldehyde, 2-[(3-methyl-2-butenyl)oxy]-

HRID 462428Notes

Reaction equation

HRID 462428 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[H-].[Na+].[CH3:12][C:13]([CH3:17])=[CH:14][CH2:15]Br>CN(C)C=O>[CH3:12][C:13]([CH3:17])=[CH:14][CH2:15][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 10702842Benzaldehyde, 2-[(3-methyl-2-butenyl)oxy]-Yield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

244 g (2 mols) of salicylaldehyde in 400 ml of dimethylformamide are added dropwise to a suspension of 60 g (2 mols) of 80% strength sodium hydride in 2,000 ml of absolute dimethylformamide, while cooling and stirring. After one hour at room temperature, 312.9 g (2.1 mols) of dimethylallyl bromide are added dropwise, again at 0° C. The mixture is stirred at room temperature overnight and thereafter the solvent is largely evaporated off and the residue is carefully hydrolyzed. The product is extracted with three 400 mL portions of methylene chloride and the combined organic phases are washed with two 400 ml portions of water. After drying over sodium sulphate and stripping off the solvent, the residue which remains is distilled in vacuo. 334.4 g (88% of theory) of 2-(3-methyl-2-butenyloxy)-benzaldehyde of boiling point 110° C./10 mm Hg are obtained.

Workup

  1. temperaturewhile cooling
  2. stirringThe mixture is stirred at room temperature overnight
  3. customthe solvent is largely evaporated off
  4. extractionThe product is extracted with three 400 mL portions of methylene chloride
  5. washthe combined organic phases are washed with two 400 ml portions of water
  6. dry with materialAfter drying over sodium sulphate
  7. distillationthe residue which remains is distilled in vacuo

Sources & evidence

ORD record
ord-9346c34765b64491b87576030f43e127
Source dataset
uspto-grants-1985_05
Patent number
US04515801

Reaction notes

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