Vanillin → 3-Methoxy-4-(4-phenylbutoxy)benzaldehyde

HRID 847281Notes

Reaction equation

HRID 847281 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[CH:5][C:4]=1[OH:11].Br[CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[C:17]1([CH2:16][CH2:15][CH2:14][CH2:13][O:11][C:4]2[CH:5]=[CH:6][C:7]([CH:9]=[O:10])=[CH:8][C:3]=2[O:2][CH3:1])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1183VanillinHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 2596681-Bromo-4-phenylbutane

Product 1

HCID 198827003-Methoxy-4-(4-phenylbutoxy)benzaldehydeYield 37.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 860 mg of vaniline, 1.00 g of 4-bromobutylbenzene, 1.00 g of potassium carbonate and 8 ml of 2-butanone was heated under reflux for 3 hours. The reaction mixture was poured into water and the product was extracted with ether. The ethereal layer was washed with water, dried and concentrated. The obtained residue was applied to silica gel column chromatography and eluted with toluene to obtain 500 mg of 4-(4-phenylbutoxy)-3-methoxybenzaldehyde.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. extractionthe product was extracted with ether
  4. washThe ethereal layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. washeluted with toluene

Sources & evidence

ORD record
ord-085e910113dd41a1a37b7ae3afb090bc
Source dataset
uspto-grants-1992_08
Patent number
US05140046

Reaction notes

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