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

HRID 1197090Notes

Reaction equation

HRID 1197090 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-0495ad0fa0dd4453b65c6833318b664a
Source dataset
uspto-grants-1992_05
Patent number
US05116853

Reaction notes

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