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

HRID 982220Notes

Reaction equation

HRID 982220 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-d09d5a45de944385b0e82adab13e0cd4
Source dataset
uspto-grants-1991_02
Patent number
US04994479

Reaction notes

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