Vanillin → 4-Cyclopentyloxy-3-methoxy-benzaldehyde

HRID 1067299Notes

Reaction equation

HRID 1067299 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[H-].[Na+].[CH:14]1(Br)[CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C)C=O>[CH:14]1([O:9][C:8]2[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=2[O:6][CH3:7])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 1183VanillinHCID 8728BromocyclopentaneHCID 24758Sodium hydride

Product 1

HCID 31527214-Cyclopentyloxy-3-methoxy-benzaldehydeYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of vanillin (50 g) in N,N-dimethylformamide (600 ml) are added 62.5% sodium hydride (13.9 g) and cyclopentyl bromide (38.8 ml) under ice-cooling, and the mixture is stirred at 90° C. overnight. The mixture is concentrated under reduced pressure to remove the N,N-dimethylformamide, and to the residue is added water. The mixture is extracted with ethyl acetate, and the extract is washed, dried, and concentrated under reduced pressure to remove the solvent. The resulting residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:1) to give 4-cyclopentyloxy-3-methoxybenzaldehyde (65 g).

Workup

  1. temperaturecooling
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove the N,N-dimethylformamide
  4. additionto the residue is added water
  5. extractionThe mixture is extracted with ethyl acetate
  6. washthe extract is washed
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove the solvent
  10. customThe resulting residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-512af14061634c70bc165893b927b165
Source dataset
uspto-grants-2001_06
Patent number
US06248743B1

Reaction notes

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