Vanillin → 4-(dodecyloxy)-3-methoxybenzaldehyde

HRID 1760895Notes

Reaction equation

HRID 1760895 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.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C(O)C>[CH2:30]([O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19]

Participants

5

Reactant 3

HCID 1183VanillinHCID 89191-BromododecaneHCID 11430Potassium Carbonate

Product 1

HCID 2875324-(dodecyloxy)-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Vanillin (100 g; 0.657 mol) is dissolved in ethanol (500 ml), and dried K2CO3 (101.5 g; 0.73 mol) is added. Heating to 80° C. is then carried out and 1-bromododecane is added dropwise under a protective gas atmosphere. The suspension is heated at reflux for a further 16 hours. After cooling to 25° C., filtration is carried out, the residue is then washed several times with ethanol and the combined filtrates are concentrated to dryness by evaporation. The residue is dissolved in tert-butyl methyl ether. Washing is then carried out with 1M aqueous sodium hydroxide solution (3×200 ml) and water (1×200 ml), and the organic phase is dried over Na2SO4, filtered off and concentrated to dryness by evaporation.

Workup

  1. temperatureThe suspension is heated
  2. temperatureat reflux for a further 16 hours
  3. temperatureAfter cooling to 25° C.
  4. filtrationfiltration
  5. washthe residue is then washed several times with ethanol
  6. concentrationthe combined filtrates are concentrated to dryness by evaporation
  7. dissolutionThe residue is dissolved in tert-butyl methyl ether
  8. washWashing
  9. dry with materialthe organic phase is dried over Na2SO4
  10. filtrationfiltered off
  11. concentrationconcentrated to dryness by evaporation

Sources & evidence

ORD record
ord-d60aaa8b09d0487e813bb6b3bf4cb49e
Source dataset
uspto-grants-2005_01
Patent number
US06846492B2

Reaction notes

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